| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:30:09 UTC |
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| Update date | 2017-01-19 02:36:20 UTC |
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| FoodComEx ID | PC000359 |
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| FoodDB Record | FDB022169 |
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| Chemical Information |
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| Name | Glucaric acid |
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| Description | Glucaric acid, also known as D-saccharic acid, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucaric acid is very soluble in water, and relatively neutral. Glucaric acid exists in all living organisms, ranging from bacteria to humans. In mammals, D-glucaric acid is an end product of the D-glucuronic acid pathway. The glucuronic acid pathway catalyzes the conversion of glucose to glucuronic acid, ascorbic acid, and pentoses. Like the pentose phosphate pathway, this pathway provides biosynthetic precursors and inter-converts some less common sugars to ones that can be metabolized. D-glucaric acid is particularly abundant in fruits and vegetables, with the highest concentrations found in grapefruits, apples, oranges, and cruciferous vegetables. The D-glucaric acid content in fruits and vegetables ranges from about 0.1 g/kg in grapes and lettuce to about 3.5 g/kg in apples and broccoli. Glucaric acid is available as a dietary supplement in the form of calcium D-glucarate and has been studied for therapeutic purposes including cholesterol reduction and cancer chemotherapy (PMID: 12747003; PMID: 18772850). Industrially, D-glucaric acid produced from oxidizing D-glucose has been successfully utilized to produce a hydroxylated nylon, resulting in a presumably biodegradable nylon fiber. Glucaric acid’s sodium salt is used in dishwasher detergents. The acid acts as a chelating agent that ties up the hard-water calcium and magnesium ions to make the detergents more efficient. Glucaric acid is also a powerful corrosion inhibitor and is used in many applications where water contacts metal surfaces. |
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| CAS Number | 25525-21-7 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioate | hmdb | | (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid | hmdb | | D-(+)-saccharate | hmdb | | D-glucosaccharate | hmdb | | D-saccharate | hmdb | | D-tetrahydroxyadipate | hmdb | | D-tetrahydroxyadipic acid | hmdb | | DL-glucaric acid | hmdb | | GKR | hmdb | | Glucarate | hmdb | | Glucosaccharic acid | hmdb | | L-gularate | hmdb | | Saccharate | Generator | | Saccharic acid | hmdb |
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| Chemical Formula | C6H10O8 |
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| IUPAC name | (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid |
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| InChI Identifier | InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1 |
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| InChI Key | DSLZVSRJTYRBFB-LLEIAEIESA-N |
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| Isomeric SMILES | O[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O |
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| Average Molecular Weight | 210.1388 |
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| Monoisotopic Molecular Weight | 210.037567296 |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | Glucuronic acid derivatives |
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| Alternative Parents | |
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| Substituents | - Glucuronic acid or derivatives
- Medium-chain hydroxy acid
- Medium-chain fatty acid
- Beta-hydroxy acid
- Hydroxy fatty acid
- Monosaccharide
- Hydroxy acid
- Dicarboxylic acid or derivatives
- Alpha-hydroxy acid
- Fatty acyl
- Fatty acid
- Secondary alcohol
- Polyol
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- 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 g |
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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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| Not Available |
