Glycolic acid (ECMDB03035) (M2MDB000475)
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 13:57:38 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:12 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Glycolic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Glycolic acid (or hydroxyacetic acid) is the smallest alpha-hydroxy acid (AHA). In its pure form, glycolic acid is a colorless crystalline solid. Due to its excellent capability to penetrate skin, glycolic acid finds applications in skin care products, most often as a chemical peel. Glycolic acid is also used for tattoo removal. In E coli it is involved in glyoxylate and dicarboxylate metabolism. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C2H4O3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 79-14-1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | 2-hydroxyacetic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | glycolic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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 |
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| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | -1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 75-80 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP Glycolic acid + Ubiquinone-8 > Glyoxylic acid + Ubiquinol-8 Glycolic acid + Menaquinone 8 > Glyoxylic acid + Menaquinol 8 2-Demethylmenaquinone 8 + Glycolic acid > 2-Demethylmenaquinol 8 + Glyoxylic acid Glyoxylic acid + Hydrogen ion + NADH > Glycolic acid + NAD Glycolaldehyde + Water + NAD > Glycolic acid +2 Hydrogen ion + NADH Phosphoglycolic acid + Water <> Glycolic acid + Phosphate + Glycolate Glycolic acid + NADP <> Glyoxylic acid + NADPH + Hydrogen ion Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide Glycolaldehyde + NAD + Water <> Glycolic acid + NADH + Hydrogen ion Phosphoglycolic acid + Water <> Glycolic acid + Phosphate Water + NAD + Glycolaldehyde > Hydrogen ion + NADH + Glycolic acid an oxidized electron acceptor + Glycolic acid > a reduced electron acceptor + Glyoxylic acid Glycolic acid + NADP < Hydrogen ion + NADPH + Glyoxylic acid Water + Phosphoglycolic acid > Glycolic acid + Phosphate Glycolaldehyde + NAD + Water > Glycolic acid + NADH Glycolic acid + NADP > Glyoxylic acid + NADPH Phosphoglycolic acid + Water > Glycolic acid + Inorganic phosphate Glycolic acid + an oxidized electron-transfer flavoprotein > Reduced acceptor + Glyoxylic acid 2 Glycolic acid + 2 an oxidized electron-transfer flavoprotein >2 Reduced acceptor +2 Glyoxylic acid Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Witzemann, Edgar J. Preparation of glycollic acid. Journal of the American Chemical Society (1917), 39 109-12. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Enzymes
- General function:
- Involved in catalytic activity
- Specific function:
- Specific function unknown
- Gene Name:
- glcD
- Uniprot ID:
- P0AEP9
- Molecular weight:
- 53811
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Acts on lactaldehyde as well as other aldehydes
- Gene Name:
- aldA
- Uniprot ID:
- P25553
- Molecular weight:
- 52272
Reactions
| (S)-lactaldehyde + NAD(+) + H(2)O = (S)-lactate + NADH. |
| Glycolaldehyde + NAD(+) + H(2)O = glycolate + NADH. |
- General function:
- Involved in catalytic activity
- Specific function:
- Specifically catalyzes the dephosphorylation of 2- phosphoglycolate. Is involved in the dissimilation of the intracellular 2-phosphoglycolate formed during the DNA repair of 3'-phosphoglycolate ends, a major class of DNA lesions induced by oxidative stress
- Gene Name:
- gph
- Uniprot ID:
- P32662
- Molecular weight:
- 27389
Reactions
| 2-phosphoglycolate + H(2)O = glycolate + phosphate. |
- General function:
- Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
- Specific function:
- Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Can also reduce 2,5-diketo-D-gluconate (25DKG) to 5-keto-D- gluconate (5KDG), 2-keto-D-gluconate (2KDG) to D-gluconate, and 2- keto-L-gulonate (2KLG) to L-idonate (IA), but it is not its physiological function. Inactive towards 2-oxoglutarate, oxaloacetate, pyruvate, 5-keto-D-gluconate, D-fructose and L- sorbose. Activity with NAD is very low
- Gene Name:
- ghrB
- Uniprot ID:
- P37666
- Molecular weight:
- 35395
Reactions
| Glycolate + NADP(+) = glyoxylate + NADPH. |
| D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H. |
| D-gluconate + NADP(+) = 2-dehydro-D-gluconate + NADPH. |
- General function:
- Involved in iron-sulfur cluster binding
- Specific function:
- Specific function unknown
- Gene Name:
- glcF
- Uniprot ID:
- P52074
- Molecular weight:
- 45110
- General function:
- Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
- Specific function:
- Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Inactive towards 2-oxo-D-gluconate, 2-oxoglutarate, oxaloacetate and pyruvate. Only D- and L-glycerate are involved in the oxidative activity with NADP. Activity with NAD is very low
- Gene Name:
- ghrA
- Uniprot ID:
- P75913
- Molecular weight:
- 35343
Reactions
| Glycolate + NADP(+) = glyoxylate + NADPH. |
| D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H. |
- General function:
- Involved in catalytic activity
- Specific function:
- Specific function unknown
- Gene Name:
- glcE
- Uniprot ID:
- P52073
- Molecular weight:
- 38361
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Transports acetate. Also able to transport glycolate
- Gene Name:
- actP
- Uniprot ID:
- P32705
- Molecular weight:
- 59197
- General function:
- Involved in lactate transmembrane transporter activity
- Specific function:
- Transports L-lactate across the membrane. Can also transport D-lactate and glycolate. Seems to be driven by a proton motive force
- Gene Name:
- lldP
- Uniprot ID:
- P33231
- Molecular weight:
- 59168
- General function:
- Involved in lactate transmembrane transporter activity
- Specific function:
- Transports glycolate across the membrane. Can also transport L-lactate and D-lactate. Seems to be driven by a proton motive force
- Gene Name:
- glcA
- Uniprot ID:
- Q46839
- Molecular weight:
- 58920
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368