Record Information |
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Version | 1.0 |
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Created at | 2020-03-18 23:22:26 UTC |
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Updated at | 2020-11-18 16:34:39 UTC |
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CannabisDB ID | CDB006171 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common 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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Structure | |
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Synonyms | Value | Source |
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D-(+)-Saccharic acid | ChEBI | D-Glucosaccharic acid | ChEBI | D-Saccharic acid | ChEBI | L-Gularic acid | ChEBI | Saccharic acid | ChEBI | D-Glucaric acid | Kegg | Glucarate | Kegg | D-(+)-Saccharate | Generator | D-Glucosaccharate | Generator | D-Saccharate | Generator | L-Gularate | Generator | Saccharate | Generator | D-Glucarate | Generator | Acid, saccharic | MeSH | Anhydrous calcium glucarate | MeSH | Anhydrous calcium saccharate | MeSH | Calcium glucarate | MeSH | Calcium glucarate, anhydrous | MeSH | Calcium saccharate | MeSH | Calcium saccharate anhydrous | MeSH | Calcium saccharate tetrahydrate | MeSH | Calcium saccharate, anhydrous | MeSH | D Glucaric acid | MeSH | D Saccharic acid | MeSH | Glucarate, anhydrous calcium | MeSH | Glucarate, calcium | MeSH | Glucosaccharic acid | MeSH | L Gularic acid | MeSH | Levo gularic acid | MeSH | Levo-gularic acid | MeSH | Saccharate tetrahydrate, calcium | MeSH | Saccharate, anhydrous calcium | MeSH | Saccharate, calcium | MeSH | Tetrahydrate, calcium saccharate | MeSH | Tetrahydroxyadipic acid | MeSH | (2R,3S,4S,5S)-2,3,4,5-Tetrahydroxyhexanedioate | HMDB | (2R,3S,4S,5S)-2,3,4,5-Tetrahydroxyhexanedioic acid | HMDB | D-Tetrahydroxyadipate | HMDB | D-Tetrahydroxyadipic acid | HMDB | DL-Glucaric acid | HMDB | GKR | HMDB |
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Chemical Formula | C6H10O8 |
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Average Molecular Weight | 210.14 |
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Monoisotopic Molecular Weight | 210.0376 |
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IUPAC Name | (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid |
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Traditional Name | saccharic acid |
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CAS Registry Number | 25525-21-7 |
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SMILES | O[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O |
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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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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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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 125-126 °C | Wikipedia | Boiling Point | Not Available | Not Available | Water Solubility | 912 mg/mL | Not Available | logP | 6.1 | Wikipedia |
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Predicted Properties | [] |
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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Glucaric acid, non-derivatized, GC-MS Spectrum | splash10-00kb-0951000000-900f03a7c305b77327a7 | Spectrum | GC-MS | Glucaric acid, non-derivatized, GC-MS Spectrum | splash10-0002-0931000000-0b5da9d9795e377e2131 | Spectrum | GC-MS | Glucaric acid, non-derivatized, GC-MS Spectrum | splash10-000w-0934000000-065f1d82bf37b3646812 | Spectrum | GC-MS | Glucaric acid, non-derivatized, GC-MS Spectrum | splash10-000t-0933000000-88564b1ce0ddb6a8ab41 | Spectrum | GC-MS | Glucaric acid, 6 TMS, GC-MS Spectrum | splash10-001l-0988100000-b295a3efe00c6ac42fb9 | Spectrum | GC-MS | Glucaric acid, non-derivatized, GC-MS Spectrum | splash10-000w-0934000000-065f1d82bf37b3646812 | Spectrum | GC-MS | Glucaric acid, non-derivatized, GC-MS Spectrum | splash10-001l-0988100000-b295a3efe00c6ac42fb9 | Spectrum | GC-MS | Glucaric acid, non-derivatized, GC-MS Spectrum | splash10-000t-0923000000-6490a1c6d0dfb83df0a3 | Spectrum | Predicted GC-MS | Glucaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05bf-9400000000-5d870077c657dc484d46 | Spectrum | Predicted GC-MS | Glucaric acid, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00b9-6011394000-83b916b3001ad13cf34d | Spectrum | Predicted GC-MS | Glucaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TBDMS_4_14, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TBDMS_5_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TBDMS_6_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, "Glucaric acid,4TBDMS,#14" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucaric acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0a4i-4290000000-dff4fd55a904d215586a | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0abi-9000000000-178202e29014c0d1d594 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0ab9-9000000000-c6d132cfd1374248952d | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0a4i-0390000000-f3fdb1545009312f6a25 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-9620000000-1bde5d31aa638eab1df1 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-052r-9000000000-fcfaa9b35c8d204ab0ec | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0ab9-9000000000-20e03e65e2d34a86ffba | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0ab9-9000000000-dd03e436136ea5ad38c4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0390000000-f3fdb1545009312f6a25 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9620000000-1bde5d31aa638eab1df1 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-052r-9000000000-fcfaa9b35c8d204ab0ec | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0ab9-9000000000-20e03e65e2d34a86ffba | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0ab9-9000000000-dd03e436136ea5ad38c4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-000i-9310000000-bd910793555bb11fd037 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0006-2960000000-b147e30a08581da98464 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-059i-9000000000-613b85fa3c0d461986b3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-000i-9310000000-ede1713559571675b04d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9530000000-87fcd3003f686bddb999 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-05fu-9000000000-7fa748efe187f8a95a86 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03dl-2950000000-4213fb06e5d54a446f19 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a70-8900000000-1c5b1e57a901b2c85510 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-9200000000-3d6d232455d3bf96a461 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a6r-8920000000-a1393eb5fa869e7c23f3 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4r-9600000000-8c43d68278949dbece7f | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ar9-9300000000-98861fb518fdc09acc58 | 2017-07-26 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, 5%_DMSO, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental) | | Spectrum |
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Pathways |
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Pathways | Not Available |
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Protein Targets |
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Enzymes | |
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Transporters | Not Available |
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Metal Bindings | Not Available |
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Receptors | Not Available |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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External Links |
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HMDB ID | HMDB0000663 |
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DrugBank ID | DB03603 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB022169 |
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KNApSAcK ID | C00052287 |
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Chemspider ID | 30577 |
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KEGG Compound ID | C00818 |
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BioCyc ID | D-GLUCARATE |
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BiGG ID | 35926 |
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Wikipedia Link | Saccharic_acid |
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METLIN ID | 5633 |
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PubChem Compound | 33037 |
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PDB ID | Not Available |
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ChEBI ID | 16002 |
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References |
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General References | - Zoltaszek R, Hanausek M, Kilianska ZM, Walaszek Z: [The biological role of D-glucaric acid and its derivatives: potential use in medicine]. Postepy Hig Med Dosw (Online). 2008 Sep 5;62:451-62. [PubMed:18772850 ]
- Singh J, Gupta KP: Calcium glucarate prevents tumor formation in mouse skin. Biomed Environ Sci. 2003 Mar;16(1):9-16. [PubMed:12747003 ]
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