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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:29 UTC

Update Date

2023-02-21 17:16:31 UTC

HMDB ID

HMDB0003052

Secondary Accession Numbers

HMDB03052

Metabolite Identification

Common Name

Lactaldehyde

Description

Lactaldehyde, also known as 2-hydroxypropanal, belongs to the class of organic compounds known as alpha-hydroxyaldehydes. These are organic compounds containing an aldehyde substituted with a hydroxyl group on the adjacent carbon. The molecule is chiral, its stereocenter being located on the second carbon atom. Lactaldehyde exists in several forms: in open-chain form and as cyclic hemiacetal; in solution and in crystal forms; as monomer and as dimer. Lactaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Lactaldehyde exists in all living species, ranging from bacteria to humans. Within humans, lactaldehyde participates in a number of enzymatic reactions. In particular, lactaldehyde can be converted into pyruvaldehyde; which is mediated by the enzyme aldose reductase. In addition, lactaldehyde can be biosynthesized from propylene glycol; which is catalyzed by the enzyme aldose reductase. Methylglyoxal is converted to D-lactaldehyde by glycerol dehydrogenase (gldA). Lactaldehyde is then oxidized to lactic acid by aldehyde dehydrogenase. In humans, lactaldehyde is involved in the metabolic disorder called the leigh syndrome pathway. Lactaldehyde is an intermediate in the methylglyoxal metabolic pathway. Lactaldehyde is a three-carbon atom species with a carbonyl group on the first carbon atom (making it an aldehyde), and a hydroxy group on the second carbon atom, making it a secondary alcohol. In crystal form, three conformers occur as hemiacetal dimers with a 1,4-dioxane ring skeleton:In equilibrium solution, negligibly small amounts of the monomer and at least one five-membered ring dimer exist.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
L-2-Hydroxypropionaldehyde	ChEBI
L-Lactaldehyde	ChEBI
(+-)-2-Hydroxypropanal	HMDB
(2S)-2-Hydroxypropanal	HMDB
(S)-Lactaldehyde	HMDB
2-Hydroxypropanal	HMDB
2-Hydroxypropionaldehyde	HMDB
alpha-Hydroxypropionaldehyde	HMDB
Hydroxypropionaldehyde	HMDB

Chemical Formula

C₃H₆O₂

Average Molecular Weight

74.0785

Monoisotopic Molecular Weight

74.036779436

IUPAC Name

(2S)-2-hydroxypropanal

Traditional Name

L-lactaldehyde

CAS Registry Number

598-35-6

SMILES

C[C@H](O)C=O

InChI Identifier

InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3/t3-/m0/s1

InChI Key

BSABBBMNWQWLLU-VKHMYHEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-hydroxyaldehydes. These are organic compounds containing an aldehyde substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydroxyaldehydes

Alternative Parents

Substituents

Alpha-hydroxyaldehyde
Secondary alcohol
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lactaldehyde (CHEBI:18041 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0003052)

Source

Endogenous

Endogenous (HMDB: HMDB0003052)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyruvate Metabolism (HMDB: HMDB0003052)
Fucose and Rhamnose Degradation (PathBank: SMP0000846)
L-Lactaldehyde Degradation (Aerobic) (PathBank: SMP0002085)
Methylglyoxal Degradation IV (PathBank: SMP0002090)
Pyruvate Metabolism (HMDB: HMDB0003052)

Disease pathway

Leigh Syndrome (PathBank: SMP0000196)
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) (PathBank: SMP0000334)
Pyruvate Dehydrogenase Complex Deficiency (PathBank: SMP0000212)
Primary Hyperoxaluria II, PH2 (PathBank: SMP0000558)
Pyruvate Kinase Deficiency (PathBank: SMP0000559)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003052)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	658 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.63	ChemAxon
logS	0.95	ALOGPS
pKa (Strongest Acidic)	14.01	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	17.91 m³·mol⁻¹	ChemAxon
Polarizability	7.16 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	113.634	31661259
DarkChem	[M-H]-	106.653	31661259
DeepCCS	[M+H]+	117.981	30932474
DeepCCS	[M-H]-	116.011	30932474
DeepCCS	[M-2H]-	151.777	30932474
DeepCCS	[M+Na]+	126.333	30932474
AllCCS	[M+H]+	122.8	32859911
AllCCS	[M+H-H2O]+	118.3	32859911
AllCCS	[M+NH4]+	127.0	32859911
AllCCS	[M+Na]+	128.2	32859911
AllCCS	[M-H]-	129.8	32859911
AllCCS	[M+Na-2H]-	135.4	32859911
AllCCS	[M+HCOO]-	141.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lactaldehyde	C[C@H](O)C=O	1196.8	Standard polar	33892256
Lactaldehyde	C[C@H](O)C=O	572.6	Standard non polar	33892256
Lactaldehyde	C[C@H](O)C=O	606.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lactaldehyde,1TMS,isomer #1	C[C@@H](C=O)O[Si](C)(C)C	829.4	Semi standard non polar	33892256
Lactaldehyde,1TMS,isomer #2	CC(O)=CO[Si](C)(C)C	926.3	Semi standard non polar	33892256
Lactaldehyde,2TMS,isomer #1	CC(=CO[Si](C)(C)C)O[Si](C)(C)C	1052.3	Semi standard non polar	33892256
Lactaldehyde,2TMS,isomer #1	CC(=CO[Si](C)(C)C)O[Si](C)(C)C	986.6	Standard non polar	33892256
Lactaldehyde,2TMS,isomer #1	CC(=CO[Si](C)(C)C)O[Si](C)(C)C	1016.7	Standard polar	33892256
Lactaldehyde,1TBDMS,isomer #1	C[C@@H](C=O)O[Si](C)(C)C(C)(C)C	1062.2	Semi standard non polar	33892256
Lactaldehyde,1TBDMS,isomer #2	CC(O)=CO[Si](C)(C)C(C)(C)C	1149.3	Semi standard non polar	33892256
Lactaldehyde,2TBDMS,isomer #1	CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1469.6	Semi standard non polar	33892256
Lactaldehyde,2TBDMS,isomer #1	CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1442.1	Standard non polar	33892256
Lactaldehyde,2TBDMS,isomer #1	CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1345.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lactaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-056v-9000000000-fe4416498788a968e467	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lactaldehyde GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9300000000-12b08b93303d8cbf5c3a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lactaldehyde 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 - Lactaldehyde 10V, Positive-QTOF	splash10-004i-9000000000-1aa2338222aff31e5e0f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactaldehyde 20V, Positive-QTOF	splash10-056r-9000000000-c450e557b2fe7c5dc5a1	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactaldehyde 40V, Positive-QTOF	splash10-0a6r-9000000000-dceca37df952939d1084	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactaldehyde 10V, Negative-QTOF	splash10-00di-9000000000-cd6930d73efb436bc0ff	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactaldehyde 20V, Negative-QTOF	splash10-00di-9000000000-97d1b594dd3b1d9b08b8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactaldehyde 40V, Negative-QTOF	splash10-0a4i-9000000000-90fa8913085480b29a8a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactaldehyde 10V, Negative-QTOF	splash10-05fr-9000000000-518c4b32efb3532122ea	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactaldehyde 20V, Negative-QTOF	splash10-05fr-9000000000-90bd5b8f63ecfac6a42a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactaldehyde 40V, Negative-QTOF	splash10-0a4i-9000000000-23a60e5f52ca732e0f56	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactaldehyde 10V, Positive-QTOF	splash10-0a4i-9000000000-feb30b99fe1a3132abb8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactaldehyde 20V, Positive-QTOF	splash10-0a4j-9000000000-f5b28df550bdfcf22cc7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactaldehyde 40V, Positive-QTOF	splash10-052s-9000000000-db6ce3d247485bf9581b	2021-09-25	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

Mitochondria

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Pyruvate metabolism	Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03776

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

18041

Food Biomarker Ontology

Not Available

VMH ID

LALD_L

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kranz, Cyrill. Synthesis of Lactic Aldehyde. Chemicke Listy pro Vedu a Prumysl (1912), 5 323-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Chen YM, Lin EC: Dual control of a common L-1,2-propanediol oxidoreductase by L-fucose and L-rhamnose in Escherichia coli. J Bacteriol. 1984 Mar;157(3):828-32. [PubMed:6421801 ]
Casazza JP, Felver ME, Veech RL: The metabolism of acetone in rat. J Biol Chem. 1984 Jan 10;259(1):231-6. [PubMed:6706932 ]
TING SM, SELLINGER OZ, MILLER ON: THE METABOLISM OF LACTALDEHYDE. VI. THE REDUCTION OF D- AND L-LACTALDEHYDE IN RAT LIVER. Biochim Biophys Acta. 1964 Aug 26;89:217-25. [PubMed:14203169 ]
TING SM, MILLER ON, SELLINGER OZ: THE METABOLISM OF LACTALDEHYDE. VII. THE OXIDATION OF D-LACTALDEHYDE IN RAT LIVER. Biochim Biophys Acta. 1965 Mar 8;97:407-15. [PubMed:14323585 ]
Akhy MT, Brown CM, Old DC: L-Rhamnose utilisation in Salmonella typhimurium. J Appl Bacteriol. 1984 Apr;56(2):269-74. [PubMed:6373710 ]
Ros J, Aguilar J: Genetic and structural evidence for the presence of propanediol oxidoreductase isoenzymes in Escherichia coli. J Gen Microbiol. 1984 Mar;130(3):687-92. [PubMed:6427403 ]
Di Costanzo L, Gomez GA, Christianson DW: Crystal structure of lactaldehyde dehydrogenase from Escherichia coli and inferences regarding substrate and cofactor specificity. J Mol Biol. 2007 Feb 16;366(2):481-93. Epub 2006 Nov 10. [PubMed:17173928 ]
ENGLESBERG E: Physiological basis for rhamnose utilization by a mutant of Pasteurella pestis. I. Experiments with resting cells; the isolation of lactic aldehyde. J Bacteriol. 1957 Jul;74(1):8-11. [PubMed:13462953 ]
Chen YM, Chakrabarti T, Lin EC: Constitutive activation of L-fucose genes by an unlinked mutation in Escherichia coli. J Bacteriol. 1984 Aug;159(2):725-9. [PubMed:6378890 ]
SANDMAN RP, MILLER ON: Studies on the metabolism of lactaldehyde. I. Separation and determination of lactaldehyde and related 3-carbon compounds. J Biol Chem. 1958 Jan;230(1):353-9. [PubMed:13502404 ]

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

Lactaldehyde + NAD → Pyruvaldehyde + NADH + Hydrogen Ion	details
Propylene glycol + NADP → Lactaldehyde + NADPH + Hydrogen Ion	details

Enzyme Details

2. 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

Lactaldehyde + NAD → Pyruvaldehyde + NADH + Hydrogen Ion	details
Propylene glycol + NADP → Lactaldehyde + NADPH + Hydrogen Ion	details

Showing metabocard for Lactaldehyde (HMDB0003052)

MOL for HMDB0003052 (Lactaldehyde)

3D MOL for HMDB0003052 (Lactaldehyde)

3D SDF for HMDB0003052 (Lactaldehyde)

3D-SDF for HMDB0003052 (Lactaldehyde)

PDB for HMDB0003052 (Lactaldehyde)

3D PDB for HMDB0003052 (Lactaldehyde)

SMILES for HMDB0003052 (Lactaldehyde)

INCHI for HMDB0003052 (Lactaldehyde)

Structure for HMDB0003052 (Lactaldehyde)

3D Structure for HMDB0003052 (Lactaldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions

Reactions