Record Information |
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Version | 1.0 |
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Created at | 2022-03-17 20:46:23 UTC |
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Updated at | 2022-03-17 20:46:23 UTC |
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NP-MRD ID | NP0047812 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 4-O-Caffeoylshikimic acid |
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Description | 4-O-Caffeoylshikimic acid, also known as 4-O-caffeoylshikimate or isodactylifric acid, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 4-O-Caffeoylshikimic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-O-Caffeoylshikimic acid has been detected, but not quantified in, fruits and pears. 4-O-Caffeoylshikimic acid is found in Dicksonia antarctica and Sarcandra glabra. This could make 4-O-caffeoylshikimic acid a potential biomarker for the consumption of these foods. |
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Structure | OC1CC(=CC(O)C1OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(21)24-15-12(19)6-9(16(22)23)7-13(15)20/h1-6,12-13,15,17-20H,7H2,(H,22,23)/b4-2- |
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Synonyms | Value | Source |
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4-O-Caffeoylshikimate | Generator | 4-Caffeoylshikimic acid | HMDB | Isodactylifric acid | HMDB | Isodattelic acid | HMDB | 4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylate | Generator |
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Chemical Formula | C16H16O8 |
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Average Mass | 336.2934 Da |
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Monoisotopic Mass | 336.08452 Da |
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IUPAC Name | 4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylic acid |
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Traditional Name | 4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | OC1CC(=CC(O)C1OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O |
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InChI Identifier | InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(21)24-15-12(19)6-9(16(22)23)7-13(15)20/h1-6,12-13,15,17-20H,7H2,(H,22,23)/b4-2- |
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InChI Key | VTURJKQJEXSKNY-RQOWECAXSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Cinnamic acids and derivatives |
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Sub Class | Hydroxycinnamic acids and derivatives |
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Direct Parent | Coumaric acids and derivatives |
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Alternative Parents | |
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Substituents | - Coumaric acid or derivatives
- Cinnamic acid ester
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Fatty acid ester
- Phenol
- Cyclitol or derivatives
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Fatty acyl
- Benzenoid
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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