(1alpha,3R,4alpha,5R)-4-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,3,5-trihydroxycyclohexanecarboxylic acid
Basic information
- CAS
905-99-7- Standard SMILES
O=C(C=Cc1ccc(O)c(O)c1)OC1[C@H](O)CC(O)(C(=O)O)C[C@H]1O- InChIKey
GYFFKZTYYAFCTR-LGTQLRDQSA-N- Molecular formula
- C16H18O9
- Average molar mass
- 354.31 g/mol
- Monoisotopic mass
- 354.09508215
Overview
See also: Cryptochlorogenic acid (annotation moved to); 4-Caffeoylquinic acid;4-O-Caffeoylquinic acid (annotation moved to).
Names & identifiers
- Preferred name
- (1alpha,3R,4alpha,5R)-4-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,3,5-trihydroxycyclohexanecarboxylic acid
- IUPAC
- trans-(3R,5R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,3,5-trihydroxycyclohexane-1-carboxylic acid
- English name
- Cryptochlorogenic acid
- Molecular formula
- C16H18O9
- Molecular weight
- 354.31
Names & synonyms
(1alpha,3R,4alpha,5R)-4-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,3,5-trihydroxycyclohexanecarboxylic acidQuinic acid, 4-caffeoyl-, E-SCHEMBL18317148DTXSID601319036AKOS030228649SY107572C3898(1S,3R,4S,5R)-4-((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,3,5-trihydroxycyclohexane-1-carboxylic acid(1S,3R,4S,5R)-4-{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexane-1-carboxylic acid4-Caffeoylquinic acidCryptochlorogenin Acid4-Dicaffeoylquinic Acid
Show more names
Cryptophyllinic acidCryptochlorogenic acidQuinic acid 4-O-caffeateCryptochlorogenic acid-RMCryptochlorogenic acid(4')4-O-trans-caffeoylquinicaci4-O-trans-caffeoylquinic acid
Properties
Computed structural properties
- XLogP
- -0.4
- Topological polar surface area
- 165 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 5
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 520
Physicochemical properties
- Boiling point
- 694.9 · 694.9±55.0 °C(Predicted)
- Density
- 1.65 · 1.65
- storage temp.
- 2 · 2-8°C
- solubility
- 50 mg/mL · DMSO : 50 mg/mL (141.12 mM; Need ultrasonic)
- form
- Solid
- pka
- 4.07 · 4.07±0.50(Predicted)
- color
- White-pale yellow
- optical activity
- -76 · [α]/D -76.0±5.0°, c = 0.5 in H2O
- Stability
- Hygroscopic
- Major Application
- food and beverages
- InChI
- InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/t11-,12-,14-,16+/m1/s1
- InChIKey
- GYFFKZTYYAFCTR-NCZKRNLISA-N
- SMILES
- O([C@H]1[C@@H](C[C@](C[C@H]1O)(O)C(=O)O)O)C(=O)C=CC1C=CC(=C(C=1)O)O
- FDA UNII
- 23 DJ84IZ9 · F23DJ84IZ9
- UNSPSC Code
- 85151701 · 85151701
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
UsesCryptochlorogenic acid may be used as a reference standard in the determination of cryptochlorogenic acid in the leaves of Hibiscus sabdariffa using high performance liquid chromatography coupled with mass spectrometry (HPLC-MS).
Uses4-O-Caffeoylquinic acid has been used as a reference compound for the quantification in high performance liquid chromatography-diode array detector (HPLC-DAD).
General DescriptionCryptochlorogenic acid is a polyphenol, found in a variety of plants, which plays a crucial role in protection against various age-related diseases.
Additional notes
DefinitionChEBI: A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 4-hydroxy group of (+)-quinic acid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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