| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:33:31 UTC |
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| Update date | 2017-01-19 02:36:42 UTC |
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| FoodComEx ID | PC000942 |
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| FoodDB Record | FDB021997 |
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| Chemical Information |
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| Name | 2-Methylcitric acid |
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| Description | Methylcitric acid (MCA) is elevated in body fluids of patients with propionic acidaemia (PA; OMIM 232000, 232050), methylmalonic aciduria (MMA; OMIM 251000, 251120) and multiple carboxylase deficiency (OMIM 253260, 253270). MCA is formed by condensation of accumulated propionyl- CoA and oxalacetate by the enzyme si-citrate synthase (EC 4.1.3.7). MCA molecule has two stereogenic centers so that it can occur in the form of four stereoisomers. Only two stereoisomers of MCA, (2S, 3S) and (2R, 3S), were found in human urine. (PMID: 17295121) [HMDB] |
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| CAS Number | 6061-96-7 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| (2S,3S)-2-methylcitrate | hmdb | | 2-Hydroxy-1,2,3-butanetricarboxylate | Generator | | 2-hydroxy-1,2,3-butanetricarboxylic acid | hmdb | | 2-hydroxybutane-1,2,3-tricarboxylate | hmdb | | 2-hydroxybutane-1,2,3-tricarboxylic acid | hmdb | | 2-methylcitrate | hmdb | | 2-methylcitric acid | hmdb |
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| Chemical Formula | C7H10O7 |
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| IUPAC name | 2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid |
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| InChI Identifier | InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13) |
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| InChI Key | YNOXCRMFGMSKIJ-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(C(O)=O)C(O)(CC(O)=O)C(O)=O |
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| Average Molecular Weight | 206.1501 |
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| Monoisotopic Molecular Weight | 206.042652674 |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Tricarboxylic acids and derivatives |
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| Direct Parent | Tricarboxylic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Tricarboxylic acid or derivatives
- Hydroxy acid
- Alpha-hydroxy acid
- Tertiary alcohol
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | Not Available | |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 2 mg |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| Toronto Research Chemicals | M265080 |
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