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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-02-24 13:28:50 UTC

Update Date

2023-02-21 17:15:55 UTC

HMDB ID

HMDB0001881

Secondary Accession Numbers

HMDB01881

Metabolite Identification

Common Name

Propylene glycol

Description

Propylene glycol (CAS: 57-55-6), also known as 1,2-propanediol, is an organic compound (a diol alcohol), usually a tasteless, odourless, and colourless clear oily liquid that is hygroscopic and miscible with water, acetone, and chloroform. It is manufactured by the hydration of propylene oxide. Propylene glycol is used as a solvent for intravenous, oral, and topical pharmaceutical preparations It is generally considered safe. However, in large doses, it can be toxic, especially if given over a short period of time. Intravenous lorazepam contains the largest amount of propylene glycol of commonly used drugs. In adults with normal liver and kidney function, the terminal half-life of propylene glycol ranges from 1.4 to 3.3 hours. Propylene glycol is metabolized by the liver to form lactate, acetate, and pyruvate. The nonmetabolized drug is excreted in the urine mainly as the glucuronide conjugate, approximately 12 to 45 percent is excreted unchanged in urine. Renal clearance decreases as the dose administered increases (390 ml/minute/173 m2 at a dose of 5 g/day but only 144 ml/minute/173 m2 at a dose of 21 g/day). These data suggest that renal clearance declines at higher propylene glycol doses because of the saturation of proximal tubular secretion of the drug. As an acceptable level of propylene glycol has not been defined, the clinical implication of a propylene glycol level is unclear. The World Health Organization (WHO) recommends a maximum consumption of 25 mg/kg/day (1.8 g/day for a 75 kg male) of propylene glycol when used as a food additive, but this limit does not address its use as a drug solvent. No maximum dose is recommended in the literature for intravenous therapy with propylene glycol. Intoxication occurs at much higher doses than the WHO dose limit and is exclusive to pharmacologic exposure. Propylene glycol toxicity includes the development of serum hyperosmolality, lactic acidosis, and kidney failure. It has been suggested that proximal tubular necrosis is the cause of acute kidney injury from propylene glycol. Along these lines, proximal tubular cell injury occurs in cultured human cells exposed to propylene glycol. Acute tubular necrosis was described with propylene glycol toxicity in a case of concomitant administration of intravenous lorazepam and trimethoprim sulfamethoxazole. Propylene glycol induced intoxication can also mimic sepsis or systemic inflammatory response syndrome (SIRS). Patients suspected of having sepsis with negative cultures should be evaluated for propylene glycol toxicity if they have been exposed to high dose lorazepam or other medications containing this solvent (PMID:17555487 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R)-1,2-Propanediol	ChEBI
R-1,2-PROPANEDIOL	ChEBI
(R)-Propylene glycol	ChEBI, KEGG
(-)-1,2-Propanediol	HMDB
(-)-Propylene glycol	HMDB
(2R)-1,2-Propanediol	HMDB
(2R)-Propane-1,2-diol	HMDB
(R)-(-)-1,2-Propanediol	HMDB
(R)-2-Hydroxy-1-propanol	HMDB
1,2-(RS)-Propanediol	HMDB
1,2-Dihydroxypropane	HMDB
1,2-Propanediol	HMDB
1,2-Propylene glycol	HMDB
1-Deoxy-sn-glycerol	HMDB
2,3-Propanediol	HMDB
2-Hydroxypropanol	HMDB
D-(-)-Propanediol	HMDB
Isopropylene glycol	HMDB
Methylethyl glycol	HMDB
Methylethylene glycol	HMDB
Monopropylene glycol	HMDB
Propylene glycol	HMDB
R-(-)-1,2-Propanediol	HMDB
R-(-)-Propylene glycol	HMDB
alpha-Propylene glycol	HMDB
α-Propylene glycol	HMDB

Chemical Formula

C₃H₈O₂

Average Molecular Weight

76.0944

Monoisotopic Molecular Weight

76.0524295

IUPAC Name

(2R)-propane-1,2-diol

Traditional Name

R-1,2-propanediol

CAS Registry Number

4254-14-2

SMILES

C[C@@H](O)CO

InChI Identifier

InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m1/s1

InChI Key

DNIAPMSPPWPWGF-GSVOUGTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

1,2-diols

Alternative Parents

Substituents

Secondary alcohol
1,2-diol
Hydrocarbon derivative
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

propane-1,2-diol (CHEBI:28972 )

Ontology

Physiological effect

Health effect

Respiratory system disorder

Pulmonary disorder

Lung Cancer (HMDB: HMDB0001881)

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Cirrhosis (HMDB: HMDB0001881)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 3426740)
Cerebrospinal Fluid (CSF) (PMID: 3746301)
Saliva (PMID: 12097436)
Cerebrospinal fluid (HMDB: HMDB0001881)

Cell

Hematocyte

Platelet (HMDB: HMDB0001881)

Tissue substructure

Muscle (HMDB: HMDB0001881)

Organ

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0001881)

Epithelium

Epidermis (HMDB: HMDB0001881)

Excreta

Biofluid or Excreta

Urine (PMID: 18953024)
Feces (PMID: 24628373)
Sweat (PMID: 22194922)
Breath (PMID: 23277518)

Cellular substructure

Cytoplasm (HMDB: HMDB0001881)
Extracellular (HMDB: HMDB0001881)

Stratum Corneum (HMDB: HMDB0001881)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001881)

Source

Exogenous

Exogenous (HMDB: HMDB0001881)

Food

Food (HMDB: HMDB0001881)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Vegetable

Mushroom

Synthetic

Personal care products

Personal care products (HMDB: HMDB0001881)

Endogenous

Plant

Plant (HMDB: HMDB0001881)
Poaceae (HMDB: HMDB0001881)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyruvate Metabolism (HMDB: HMDB0001881)
Pyruvate Metabolism (HMDB: HMDB0001881)

Disease pathway

Leigh Syndrome (PathBank: SMP0120726)
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) (PathBank: SMP0120533)
Pyruvate Kinase Deficiency (PathBank: SMP0120623)
Primary Hyperoxaluria II, PH2 (PathBank: SMP0120841)
Pyruvate Dehydrogenase Complex Deficiency (PathBank: SMP0120531)

Asthma (HMDB: HMDB0001881)

Role

Industrial application

Personal care product

Personal care product (HMDB: HMDB0001881)
Cosmetic (HMDB: HMDB0001881)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001881)

Biomarker

Preeclampsia/Eclampsia (HMDB: HMDB0001881)
Pregnancy (HMDB: HMDB0001881)
Cirrhosis (HMDB: HMDB0001881)

Food and nutrition

Food and nutrition (HMDB: HMDB0001881)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-60 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL at 20 °C	Not Available
LogP	-0.92	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	952 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.79	ChemAxon
logS	1.1	ALOGPS
pKa (Strongest Acidic)	14.47	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	18.97 m³·mol⁻¹	ChemAxon
Polarizability	8.01 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	119.194	30932474
DeepCCS	[M-H]-	116.758	30932474
DeepCCS	[M-2H]-	152.931	30932474
DeepCCS	[M+Na]+	127.628	30932474
AllCCS	[M+H]+	123.0	32859911
AllCCS	[M+H-H2O]+	118.6	32859911
AllCCS	[M+NH4]+	127.2	32859911
AllCCS	[M+Na]+	128.4	32859911
AllCCS	[M-H]-	131.2	32859911
AllCCS	[M+Na-2H]-	136.8	32859911
AllCCS	[M+HCOO]-	143.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Propylene glycol	C[C@@H](O)CO	1505.0	Standard polar	33892256
Propylene glycol	C[C@@H](O)CO	711.0	Standard non polar	33892256
Propylene glycol	C[C@@H](O)CO	735.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Propylene glycol,1TMS,isomer #1	C[C@H](CO)O[Si](C)(C)C	848.9	Semi standard non polar	33892256
Propylene glycol,1TMS,isomer #2	C[C@@H](O)CO[Si](C)(C)C	857.7	Semi standard non polar	33892256
Propylene glycol,2TMS,isomer #1	C[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	999.7	Semi standard non polar	33892256
Propylene glycol,1TBDMS,isomer #1	C[C@H](CO)O[Si](C)(C)C(C)(C)C	1082.8	Semi standard non polar	33892256
Propylene glycol,1TBDMS,isomer #2	C[C@@H](O)CO[Si](C)(C)C(C)(C)C	1081.2	Semi standard non polar	33892256
Propylene glycol,2TBDMS,isomer #1	C[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1427.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Propylene glycol GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014j-0900000000-d90655d5a614c4ddf998	2020-03-26	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Propylene glycol GC-MS (2 TMS)	splash10-014i-1900000000-ab4a1ff05d1275711170	2020-03-26	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Propylene glycol EI-B (Non-derivatized)	splash10-0002-9000000000-a18bede40461dace657b	2020-03-26	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Propylene glycol EI-B (Non-derivatized)	splash10-0002-9000000000-6d2345a66e2cf8d2d379	2020-03-26	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Propylene glycol GC-EI-TOF (Non-derivatized)	splash10-014j-0900000000-d90655d5a614c4ddf998	2020-03-26	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Propylene glycol GC-MS (Non-derivatized)	splash10-014i-1900000000-ab4a1ff05d1275711170	2020-03-26	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propylene glycol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-cbc512db1a4c5510015e	2020-03-26	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Propylene glycol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a7i-9000000000-6c96c59f8ba2e0e5353e	2020-03-26	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Propylene glycol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-005d-9000000000-ae07e4049d24341335ec	2020-03-26	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Propylene glycol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00aj-9000000000-f455f8f0f79f9970711a	2020-03-26	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Propylene glycol EI-B (HITACHI RMU-7M) , Positive-QTOF	splash10-0002-9000000000-c5bf57086deb14e12495	2020-03-26	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Propylene glycol EI-B (HITACHI M-80B) , Positive-QTOF	splash10-0002-9000000000-6d2345a66e2cf8d2d379	2020-03-26	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 10V, Positive-QTOF	splash10-004i-9000000000-0a1a58ae50ca7bfbc92f	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 20V, Positive-QTOF	splash10-0a6r-9000000000-4f58eaf424aa13185ca2	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 40V, Positive-QTOF	splash10-052f-9000000000-d0e5def95a7a7879dc71	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 10V, Negative-QTOF	splash10-004i-9000000000-5bf5d9d3c7cf604af9a3	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 20V, Negative-QTOF	splash10-056r-9000000000-ea5b27ac0cc585591f63	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 40V, Negative-QTOF	splash10-0a4i-9000000000-ecc48f7be3304c6cc1e0	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 10V, Negative-QTOF	splash10-0a6r-9000000000-ea4d9d80ebf7615e6811	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 20V, Negative-QTOF	splash10-0a4i-9000000000-a77309b9b0e17e94870d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 40V, Negative-QTOF	splash10-0006-9000000000-7bb23415e61ec73a459c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 10V, Positive-QTOF	splash10-0a4l-9000000000-5dba4634f494296e1347	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 20V, Positive-QTOF	splash10-0a4l-9000000000-2174cc6a153316ad8c52	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propylene glycol 40V, Positive-QTOF	splash10-0006-9000000000-a1a685f935041163641b	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2020-03-26	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 500 MHz, H₂O, experimental)	2020-03-26	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Breath
Cerebrospinal Fluid (CSF)
Feces
Saliva
Sweat
Urine

Tissue Locations

Epidermis
Intestine
Neuron
Platelet
Skeletal Muscle
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Pyruvate metabolism	Not Available
Leigh Syndrome		Not Available
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)		Not Available
Pyruvate Dehydrogenase Complex Deficiency		Not Available
Primary hyperoxaluria II, PH2		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	22.3 +/- 3.3 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.0-5.0 uM	Adult (>18 years old)	Both	Normal	3426740	details
Blood	Detected and Quantified	2.0 (0.0-5.0) uM	Adult (>18 years old)	Both	Normal	3426740	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	33 +/- 50 uM	Adult (>18 years old)	Both	Normal	18502700	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.63 +/- 0.4 (0 - 1.0) uM	Adult (>18 years old)	Not Specified	Normal	3746301	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected and Quantified	3 (<1-50) uM	Adult (>18 years old)	Male	Normal	19259987	details
Saliva	Detected and Quantified	20 (<1-178) uM	Adult (>18 years old)	Male	Normal	19259987	details
Saliva	Detected and Quantified	17 (<1-84) uM	Adult (>18 years old)	Male	Normal	19259987	details
Saliva	Detected and Quantified	8 (<1-46) uM	Adult (>18 years old)	Female	Normal	19259987	details
Saliva	Detected and Quantified	1-121 uM	Adult (>18 years old)	Male	normal	19259987	details
Saliva	Detected and Quantified	1-140 uM	Adult (>18 years old)	Male	normal	19259987	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	26.76 +/- 21.09 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	>10 uM	Adult (>18 years old)	Both	Normal	12097436	details
Sweat	Detected and Quantified	< 10 uM	Adult (60 years old)	Male	Normal	22194922	details
Sweat	Detected and Quantified	< 10 uM	Adult (40 years old)	Male	Normal	22194922	details
Urine	Detected and Quantified	20.586 +/- 22.556 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	6.7 (1.4-44.3) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	7.0 (2.9) uM	Adult (>18 years old)	Female	Down syndrome pregnancy	23313728	details
Blood	Detected and Quantified	6.6 (1.9) uM	Adult (>18 years old)	Female	Pregnancy	23313728	details
Blood	Detected and Quantified	36.3 +/- 19.9 uM	Adult (>18 years old)	Both	Heart Transplant	21359215	details
Blood	Detected and Quantified	9.66 +/- 4.10 uM	Adult (>18 years old)	Female	Pregnancy with fetuses with trisomy 18	23535240	details
Blood	Detected and Quantified	7.94 +/- 3.69 uM	Adult (>18 years old)	Female	Pregnancy	23535240	details
Blood	Detected and Quantified	9.9 (4.9) uM	Adult (>18 years old)	Female	Early preeclampsia	22494326	details
Blood	Detected and Quantified	8.0 (3.4) uM	Adult (>18 years old)	Female	Pregnancy	22494326	details
Blood	Detected and Quantified	8.84 (2.78) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	8.25 (2.09) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	11.1 (5.0) uM	Adult (>18 years old)	Female	Late-onset preeclampsia	23159745	details
Blood	Detected and Quantified	11.8 (4.9) uM	Adult (>18 years old)	Female	Pregnancy	23159745	details
Blood	Detected and Quantified	15.0 (5.0-35.4) uM	Adult (>18 years old)	Both	Cirrhosis	3426740	details
Breath	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Asthma	23277518	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Urine	Detected and Quantified	2.0 (0.0-31.0) umol/mmol creatinine	Not Specified	Both	Lung cancer	18953024	details
Urine	Detected and Quantified	150.63 +/- 491.323 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Cirrhosis
Casazza JP, Frietas J, Stambuk D, Morgan MY, Veech RL: The measurement of 1,2-propanediol, D, L-2,3-butanediol and meso-2,3-butanediol in controls and alcoholic cirrhotics. Alcohol Alcohol Suppl. 1987;1:607-9. [PubMed:3426740 ]
Early preeclampsia
Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
Pregnancy
Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ] Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ] Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ] Bahado-Singh RO, Akolekar R, Chelliah A, Mandal R, Dong E, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester trisomy 18 detection. Am J Obstet Gynecol. 2013 Jul;209(1):65.e1-9. doi: 10.1016/j.ajog.2013.03.028. Epub 2013 Mar 25. [PubMed:23535240 ] Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Late-onset preeclampsia
Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
Asthma
van de Kant KD, van Berkel JJ, Jobsis Q, Lima Passos V, Klaassen EM, van der Sande L, van Schayck OC, de Jongste JC, van Schooten FJ, Derks E, Dompeling E, Dallinga JW: Exhaled breath profiling in diagnosing wheezy preschool children. Eur Respir J. 2013 Jan;41(1):183-8. doi: 10.1183/09031936.00122411. [PubMed:23277518 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Lung Cancer
Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

600807 (Asthma)
114500 (Colorectal cancer)
211980 (Lung Cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB02159

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Propylene_glycol

METLIN ID

Not Available

PubChem Compound

259994

PDB ID

Not Available

ChEBI ID

28972

Food Biomarker Ontology

Not Available

VMH ID

12PPD_R

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Tuck, Michael William Marshall. Preparation of propylene glycol by hydrogenation of glycerol. PCT Int. Appl. (2008), 20pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
Brucks R, Nanavaty M, Jung D, Siegel F: The effect of ultrasound on the in vitro penetration of ibuprofen through human epidermis. Pharm Res. 1989 Aug;6(8):697-701. [PubMed:2813262 ]
Claverie F, Giordano-Labadie F, Bazex J: [Contact eczema induced by propylene glycol. Concentration and vehicle adapted for for patch tests]. Ann Dermatol Venereol. 1997;124(4):315-7. [PubMed:9739936 ]
Li N, Liu Z, Jia X, Cui W, Wang W, Zhang X, Han C, Chen J, Wang M: [Study on the toxicological effect of chloropropanols on rats]. Wei Sheng Yan Jiu. 2003 Jul;32(4):349-52. [PubMed:14535099 ]
Maltaris T, Dimmler A, Muller A, Binder H, Hoffmann I, Kohl J, Siebzehnrubl E, Beckmann MW, Dittrich R: The use of an open-freezing system with self-seeding for cryopreservation of mouse ovarian tissue. Reprod Domest Anim. 2005 Jun;40(3):250-4. [PubMed:15943700 ]
Li GL, van der Geest R, Chanet L, van Zanten E, Danhof M, Bouwstra JA: In vitro iontophoresis of R-apomorphine across human stratum corneum. Structure-transport relationship of penetration enhancement. J Control Release. 2002 Nov 7;84(1-2):49-57. [PubMed:12399167 ]
Fare JC, Guesnon P, Helouis JJ, Normand S, Andre JL, Duvaldestin P: [Intramuscular premedication with diazepam in a fat emulsion]. Cah Anesthesiol. 1984 May-Jun;32(4):303-6. [PubMed:6529665 ]
Reichard GA Jr, Skutches CL, Hoeldtke RD, Owen OE: Acetone metabolism in humans during diabetic ketoacidosis. Diabetes. 1986 Jun;35(6):668-74. [PubMed:3086164 ]
Casazza JP, Frietas J, Stambuk D, Morgan MY, Veech RL: The measurement of 1,2-propanediol, D, L-2,3-butanediol and meso-2,3-butanediol in controls and alcoholic cirrhotics. Alcohol Alcohol Suppl. 1987;1:607-9. [PubMed:3426740 ]
Vaddi HK, Ho PC, Chan YW, Chan SY: Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum. Biol Pharm Bull. 2003 Feb;26(2):220-8. [PubMed:12576684 ]
Fernandez C, Marti-Mestres G, Ramos J, Maillols H: LC analysis of benzophenone-3: II application to determination of 'in vitro' and 'in vivo' skin penetration from solvents, coarse and submicron emulsions. J Pharm Biomed Anal. 2000 Dec;24(1):155-65. [PubMed:11108549 ]
Vaddi HK, Ho PC, Chan SY: Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, Fourier transform infrared spectroscopy, and differential scanning calorimetry. J Pharm Sci. 2002 Jul;91(7):1639-51. [PubMed:12115825 ]
Gancevici GG: Role of complement inhibition in topical therapy of muco-cutaneous herpes simplex virus infections. Roum Arch Microbiol Immunol. 1993 Oct-Dec;52(4):293-303. [PubMed:7827366 ]
Liu JH, Gao D, He LQ, Moey LK, Hua K, Liu ZB: The phase diagram for the ternary system propylene glycol-sodium chloride-water and their application to platelet cryopreservation. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2003 Feb;11(1):92-5. [PubMed:12667299 ]
Rajasenan RS, Riley RJ, Leeder JS: Expression and inducibility of antigens in severe combined immunodeficient mice recognized by human anti-P450 antibodies. Toxicol Appl Pharmacol. 1995 Nov;135(1):89-99. [PubMed:7482543 ]
Decherchi P, Lammari-Barreault N, Cochard P, Carin M, Rega P, Pio J, Pellissier JF, Ladaique P, Novakovitch G, Gauthier P: CNS axonal regeneration with peripheral nerve grafts cryopreserved by vitrification: cytological and functional aspects. Cryobiology. 1997 May;34(3):214-39. [PubMed:9160994 ]
Trottet L, Owen H, Holme P, Heylings J, Collin IP, Breen AP, Siyad MN, Nandra RS, Davis AF: Are all aciclovir cream formulations bioequivalent? Int J Pharm. 2005 Nov 4;304(1-2):63-71. Epub 2005 Sep 1. [PubMed:16139970 ]
Miller DL, Wildnauer RH: Thermoanalytical probes for the analysis of physical properties of stratum corneum. J Invest Dermatol. 1977 Sep;69(3):287-9. [PubMed:894064 ]
Zar T, Graeber C, Perazella MA: Recognition, treatment, and prevention of propylene glycol toxicity. Semin Dial. 2007 May-Jun;20(3):217-9. [PubMed:17555487 ]

Enzymes

Enzyme Details

1. Aldose reductase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:: AKR1B1
Uniprot ID:: P15121
Molecular weight:: 35853.125

Reactions

Propylene glycol + NADP → Lactaldehyde + NADPH + Hydrogen Ion	details

Enzyme Details

2. Coagulation factor XIII A chain

General function:: Involved in protein-glutamine gamma-glutamyltransferase activity
Specific function:: Factor XIII is activated by thrombin and calcium ion to a transglutaminase that catalyzes the formation of gamma-glutamyl-epsilon-lysine cross-links between fibrin chains, thus stabilizing the fibrin clot. Also cross-link alpha-2-plasmin inhibitor, or fibronectin, to the alpha chains of fibrin.
Gene Name:: F13A1
Uniprot ID:: P00488
Molecular weight:: 83267.785

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

3. Aldo-keto reductase family 1 member B10

General function:: Not Available
Specific function:: Acts as all-trans-retinaldehyde reductase. Can efficiently reduce aliphatic and aromatic aldehydes, and is less active on hexoses (in vitro). May be responsible for detoxification of reactive aldehydes in the digested food before the nutrients are passed on to other organs.
Gene Name:: AKR1B10
Uniprot ID:: O60218
Molecular weight:: Not Available

Reactions

Propylene glycol + NADP → Lactaldehyde + NADPH + Hydrogen Ion	details

Showing metabocard for Propylene glycol (HMDB0001881)

MOL for HMDB0001881 (Propylene glycol)

3D MOL for HMDB0001881 (Propylene glycol)

3D SDF for HMDB0001881 (Propylene glycol)

3D-SDF for HMDB0001881 (Propylene glycol)

PDB for HMDB0001881 (Propylene glycol)

3D PDB for HMDB0001881 (Propylene glycol)

SMILES for HMDB0001881 (Propylene glycol)

INCHI for HMDB0001881 (Propylene glycol)

Structure for HMDB0001881 (Propylene glycol)

3D Structure for HMDB0001881 (Propylene glycol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

References

Reactions