glycolic acid (YMDB00807)

Identification

YMDB ID

YMDB00807

Name

glycolic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Glycolic acid, also known as 2-hydroxyacetate or glycolate, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. Glycolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycolic acid exists in all living species, ranging from bacteria to humans. Glycolic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2-Hydroxyacetate
2-Hydroxyacetic acid
a-Hydroxyacetate
a-Hydroxyacetic acid
Acetic acid, hydroxy-
alpha-Hydroxyacetate
alpha-Hydroxyacetic acid
Glycocide
Glycolate
Glycolic acid
Glycollate
Glycollic acid
Hydroxyacetate
hydroxyacetic acid
Hydroxyethanoate
Hydroxyethanoic acid
Kyselina glykolova
Kyselina hydroxyoctova
Polyglycolic acid
Sodium glycolate
2-Hydroxyethanoic acid
HOCH2COOH
2-Hydroxyethanoate
Α-hydroxyacetate
Α-hydroxyacetic acid
GlyPure
GlyPure 70
Glycolic acid, 2-(14)C-labeled
Glycolic acid, 1-(14)C-labeled
Glycolic acid, potassium salt
Glycolic acid, monopotassium salt
Glycolic acid, calcium salt
Glycolic acid, monoammonium salt
Glycolic acid, monolithium salt
Glycolic acid, monosodium salt
Potassium glycolate

CAS number

79-14-1

Weight

Average: 76.0514
Monoisotopic: 76.016043994

InChI Key

AEMRFAOFKBGASW-UHFFFAOYSA-N

InChI

InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)

IUPAC Name

2-hydroxyacetic acid

Traditional IUPAC Name

glycolic acid

Chemical Formula

C₂H₄O₃

SMILES

OCC(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents

Substituents

Alpha-hydroxy acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:17497 )
2-hydroxy monocarboxylic acid (CHEBI:17497 )

Physical Properties

State

Solid

Charge

Melting point

75-80 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	-1.11 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	608 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1	ChemAxon
logS	0.9	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	14.35 m³·mol⁻¹	ChemAxon
Polarizability	6.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Glyoxylate and dicarboxylate metabolism

ec00630

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-cadf899be6b15d008330	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-e66ed28d8419895e0fb4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0900000000-7f84fac3284d17fa3ba6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-d724c85a3b30e3c2e4bc	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7l-9000000000-1e9466549305eb20257b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05i9-9520000000-5f0019fe63eb6e692109	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-004i-9000000000-e942bdae1d60e5f5d649	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9000000000-f225de2de3540c3f50a4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00di-9000000000-7de217d97b44f53aad82	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-88af2b259f82cd1d8938	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-c968a24f0640b154325b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-88af2b259f82cd1d8938	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-c968a24f0640b154325b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 1V, positive	splash10-004i-9000000000-fa715ee3ce9abbc94edb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 2V, positive	splash10-004i-9000000000-ace3c5f526d28fd24de9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 3V, positive	splash10-004i-9000000000-ff7f922c2460adb6a10d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-004i-9000000000-1d63aaaf9cbc6d3bb3b4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-004j-9000000000-e9c74e7df728e016450c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-002b-9000000000-d0963403f3a8ff9e576d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 7V, positive	splash10-002b-9000000000-9e1d6b2e2b889232d610	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0002-9000000000-e9824f68b2176db90d33	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 9V, positive	splash10-000t-9000000000-02329982bc7150d972bf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 10V, positive	splash10-000t-9000000000-216d8ece56b0a44e5289	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-d961c3c14ec415e3141e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-67f73be970ba9f885c4a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-7445713a5fe347bbc8b8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-26e13242443efc1aa846	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-6ba976b949118cd0a86a	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-2885890e3bb8c015742f	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828

Synthesis Reference:

Witzemann, Edgar J. Preparation of glycollic acid. Journal of the American Chemical Society (1917), 39 109-12.

External Links:

Resource	Link
CHEBI ID	17497
HMDB ID	HMDB00115
Pubchem Compound ID	757
Kegg ID	C00160
ChemSpider ID	737
FOODB ID	FDB003298
Wikipedia	Glycolic_acid
BioCyc ID	GLYCOLLATE

Enzymes

Protein Details

1. Enolase-phosphatase E1

General function:: Involved in catalytic activity
Specific function:: Bifunctional enzyme that catalyzes the enolization of 2,3-diketo-5-methylthiopentyl-1-phosphate (DK-MTP-1-P) into the intermediate 2-hydroxy-3-keto-5-methylthiopentenyl-1-phosphate (HK-MTPenyl-1-P), which is then dephosphorylated to form the acireductone 1,2-dihydroxy-3-keto-5-methylthiopentene (DHK-MTPene)
Gene Name:: UTR4
Uniprot ID:: P32626
Molecular weight:: 25187.19922

Reactions

5-(methylthio)-2,3-dioxopentyl phosphate + H(2)O → 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + phosphate.
2-Phosphoglycolate + H2O → glycolate + phosphate

Protein Details

2. Putative 2-hydroxyacid dehydrogenase YNL274C

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Not Available
Gene Name:: Not Available
Uniprot ID:: P53839
Molecular weight:: 38831.19922

Reactions

glycolate + NADP+ → glyoxylate + NADPH + H+.

Protein Details

3. Putative uncharacterized hydrolase YOR131C

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: Not Available
Uniprot ID:: Q12486
Molecular weight:: 24839.80078

Reactions

2-Phosphoglycolate + H2O → glycolate + phosphate

Protein Details

4. Uncharacterized protein YMR130W

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: Not Available
Uniprot ID:: Q04223
Molecular weight:: 35278.10156

Reactions

2-Phosphoglycolate + H2O → glycolate + phosphate

Structure for #<Compound:0xa33aede8>

Enzymes

Reactions

Reactions

Reactions

Reactions