Record Information |
---|
Version | 1.0 |
---|
Created at | 2021-11-12 23:46:50 UTC |
---|
Updated at | 2021-11-26 17:44:44 UTC |
---|
NP-MRD ID | NP0044040 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | 1,5-O-Dicaffeoylquinic acid |
---|
Description | 1,5-Dicaffeoylquinic acid, also known as cinarin or cynarex, belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1. It was first documented in 2002 (PMID: 12494749). 1,5-Dicaffeoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). |
---|
Structure | O[C@@H]1C[C@](C[C@@H](OC(=O)C=CC2=CC=C(O)C(O)=C2)[C@H]1O)(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=O InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/t19-,20-,23+,25-/m1/s1 |
---|
Synonyms | Value | Source |
---|
1,5-Dicaffeoylquinate | Generator | Cynarex | MeSH | Cinarin | MeSH | Cynarin, (1alpha,3alpha,4alpha,5beta)-isomer | MeSH | 1-Carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate) | MeSH | Cinarina | MeSH | Cynarix | MeSH | Cynarine | MeSH | Listrocol | MeSH | Nivellipid | MeSH | Phemocil | MeSH | Listricol | MeSH | Cynarin | MeSH | Cinarine | MeSH | 1,5-Dicaffeoylquinic acid | MeSH |
|
---|
Chemical Formula | C25H24O12 |
---|
Average Mass | 516.4550 Da |
---|
Monoisotopic Mass | 516.12678 Da |
---|
IUPAC Name | (1R,3R,4S,5R)-1,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid |
---|
Traditional Name | (1R,3R,4S,5R)-1,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | O[C@@H]1C[C@](C[C@@H](OC(=O)C=CC2=CC=C(O)C(O)=C2)[C@H]1O)(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=O |
---|
InChI Identifier | InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/t19-,20-,23+,25-/m1/s1 |
---|
InChI Key | YDDUMTOHNYZQPO-GCBRTHAASA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 1H NMR Spectrum (1D, 300 MHz, Deuterium oxide, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Deuterium oxide, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Deuterium oxide, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Deuterium oxide, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Deuterium oxide, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Deuterium oxide, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Deuterium oxide, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Deuterium oxide, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Deuterium oxide, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Deuterium oxide, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | Eleutherococcus senticosus |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Alcohols and polyols |
---|
Direct Parent | Quinic acids and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Quinic acid
- Cinnamic acid or derivatives
- Coumaric acid or derivatives
- Cinnamic acid ester
- Hydroxycinnamic acid or derivatives
- Tricarboxylic acid or derivatives
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Cyclohexanol
- Phenol
- Fatty acid ester
- Monocyclic benzene moiety
- Fatty acyl
- Benzenoid
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- 1,2-diol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Aromatic homomonocyclic compound
|
---|
Molecular Framework | Aromatic homomonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|