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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:51:15 UTC

Update Date

2023-02-21 17:26:56 UTC

HMDB ID

HMDB0039407

Secondary Accession Numbers

HMDB39407

Metabolite Identification

Common Name

Methyl (±)-3-hydroxyhexanoate

Description

Methyl (±)-3-hydroxyhexanoate, also known as methyl-b-hydroxyhexanoic acid or fema 3508, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Methyl (±)-3-hydroxyhexanoate is found, on average, in the highest concentration within pineapples (Ananas comosus). This could make methyl (±)-3-hydroxyhexanoate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Methyl (±)-3-hydroxyhexanoate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl (±)-3-hydroxyhexanoic acid	Generator
FEMA 3508	HMDB
Hexanoic acid, 3-hydroxy-, methyl ester	HMDB
Methyl 3-hydroxycaproate	HMDB
Methyl 3-hydroxyhexanoate	HMDB
Methyl 3-hydroxyhexanoic acid	HMDB
Methyl-b-hydroxyhexanoate	HMDB
Methyl-b-hydroxyhexanoic acid	HMDB
Methyl-beta-hydroxyhexanoic acid	HMDB
Methyl-β-hydroxyhexanoate	HMDB
Methyl-β-hydroxyhexanoic acid	HMDB

Chemical Formula

C₇H₁₄O₃

Average Molecular Weight

146.1843

Monoisotopic Molecular Weight

146.094294314

IUPAC Name

methyl 3-hydroxyhexanoate

Traditional Name

methyl 3-hydroxyhexanoate

CAS Registry Number

21188-58-9

SMILES

CCCC(O)CC(=O)OC

InChI Identifier

InChI=1S/C7H14O3/c1-3-4-6(8)5-7(9)10-2/h6,8H,3-5H2,1-2H3

InChI Key

ACCRBMDJCPPJDX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Fatty acid ester
Fatty acid methyl ester
Fatty acyl
Methyl ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039407)
Cytoplasm (HMDB: HMDB0039407)

Source

Exogenous

Exogenous (HMDB: HMDB0039407)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	220.00 to 221.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	52980 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.607 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	97.1 g/L	ALOGPS
logP	0.82	ALOGPS
logP	0.73	ChemAxon
logS	-0.18	ALOGPS
pKa (Strongest Acidic)	15	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	37.36 m³·mol⁻¹	ChemAxon
Polarizability	16.02 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
DarkChem	[M+H]+	132.93	31661259
DarkChem	[M-H]-	130.815	31661259
DeepCCS	[M+H]+	128.201	30932474
DeepCCS	[M-H]-	124.865	30932474
DeepCCS	[M-2H]-	161.462	30932474
DeepCCS	[M+Na]+	136.95	30932474
AllCCS	[M+H]+	136.5	32859911
AllCCS	[M+H-H2O]+	132.4	32859911
AllCCS	[M+NH4]+	140.2	32859911
AllCCS	[M+Na]+	141.3	32859911
AllCCS	[M-H]-	134.2	32859911
AllCCS	[M+Na-2H]-	136.6	32859911
AllCCS	[M+HCOO]-	139.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl (??)-3-hydroxyhexanoate	CCCC(O)CC(=O)OC	1738.1	Standard polar	33892256
Methyl (??)-3-hydroxyhexanoate	CCCC(O)CC(=O)OC	1043.9	Standard non polar	33892256
Methyl (??)-3-hydroxyhexanoate	CCCC(O)CC(=O)OC	1121.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl (??)-3-hydroxyhexanoate,1TMS,isomer #1	CCCC(CC(=O)OC)O[Si](C)(C)C	1183.5	Semi standard non polar	33892256
Methyl (??)-3-hydroxyhexanoate,1TBDMS,isomer #1	CCCC(CC(=O)OC)O[Si](C)(C)C(C)(C)C	1392.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl (±)-3-hydroxyhexanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9100000000-76ce6b24ff6c91c1b118	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl (±)-3-hydroxyhexanoate GC-MS (1 TMS) - 70eV, Positive	splash10-009f-9400000000-e0559745335a70b91aa8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl (±)-3-hydroxyhexanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl (±)-3-hydroxyhexanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 10V, Positive-QTOF	splash10-002b-3900000000-638451cc2f9adccc74e2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 20V, Positive-QTOF	splash10-00mk-9600000000-f78c507102fb2592b5b6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 40V, Positive-QTOF	splash10-0006-9000000000-4cc7deef173d62a94605	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 10V, Negative-QTOF	splash10-0002-2900000000-36828f7c5bd2b027303b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 20V, Negative-QTOF	splash10-01vk-9700000000-14c3c73162b281952bc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 40V, Negative-QTOF	splash10-0006-9000000000-d8a6d6569dd1f366079a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 10V, Positive-QTOF	splash10-0avj-9200000000-36745011f80d48b7e799	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 20V, Positive-QTOF	splash10-0a4l-9000000000-534ff809617191d0575a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 40V, Positive-QTOF	splash10-0a4l-9000000000-a61fae1aab19796290ea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 10V, Negative-QTOF	splash10-0002-4900000000-1fa615ba849c2b95e974	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 20V, Negative-QTOF	splash10-006x-9200000000-cbc89d9297e003b93cb7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (±)-3-hydroxyhexanoate 40V, Negative-QTOF	splash10-0006-9000000000-1b4e0b4165b7a7f81e9b	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003805

KNApSAcK ID

Not Available

Chemspider ID

453451

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

519845

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036571

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methyl (±)-3-hydroxyhexanoate (HMDB0039407)

MOL for HMDB0039407 (Methyl (±)-3-hydroxyhexanoate)

3D MOL for HMDB0039407 (Methyl (±)-3-hydroxyhexanoate)

3D SDF for HMDB0039407 (Methyl (±)-3-hydroxyhexanoate)

3D-SDF for HMDB0039407 (Methyl (±)-3-hydroxyhexanoate)

PDB for HMDB0039407 (Methyl (±)-3-hydroxyhexanoate)

3D PDB for HMDB0039407 (Methyl (±)-3-hydroxyhexanoate)

SMILES for HMDB0039407 (Methyl (±)-3-hydroxyhexanoate)

INCHI for HMDB0039407 (Methyl (±)-3-hydroxyhexanoate)

Structure for HMDB0039407 (Methyl (±)-3-hydroxyhexanoate)

3D Structure for HMDB0039407 (Methyl (±)-3-hydroxyhexanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra