CRYPTOCHLOROGENIC ACID

Synonyms. Cryptochlorogenic acid; 4-O-Caffeoylquinic acid; 4-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid; (3S,5S)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxycyclohexane-1- carboxylic acid; 3,4-Dihydroxycinnamic acid 4-carboxy-2,4,6-trihydroxycyclohexyl ester; (1alpha,3alpha,4alpha, 5beta) -4- (3-(3,4-(Dihydroxyphenyl) -1-oxo-2-propenyl)oxy)-1,3,5- trihydroxy cyclohexanecarboxylic acid;

CRYPTOCHLOROGENIC ACID

Click for original image

 

PRODUCT IDENTIFICATION

CAS RN

905-99-7

EINECS RN

 

FORMULA

 C16H18O9

MOLE WEIGHT

354.31

H.S CODE

 2918.29.6500

SMILES

 C1[C@@H](C([C@H](CC1(C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C= C2 )O)O)O

CLASSIFICATION

Hydroxycinnamic acid, Choleretic

EXTRA NOTES

 Cryptochlorogenic acid (4-O-Caffeoylquinic acid) is an isomer of chlorogenic acid and possesses antioxidant properties.

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

white powder

MELTING POINT

182 ~ 184 C

BOILING POINT

 

DENSITY

1.65

SOLUBILITY IN WATER

Soluble in hot water

SOLVENT SOLUBILITY Soluble in alcohol

VAPOR DENSITY

 

log P(octanol-water)

  

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pK

 

REFRACTIVE INDEX

 

FLASH POINT

 

 
STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents.

POLYMERIZATION

Has not been reported

NFPA RATINGS

Health: 1, Flammability: 0, Reactivity: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Cryptochlorogenic acid

Google Scholar Search - 4-O-Caffeoylquinic acid

Drug Information Portal (U.S. National Library of Medicine) - Cryptochlorogenic acid

PubChem Compound Summary - Cryptochlorogenic acid

KEGG (Kyoto Encyclopedia of Genes and Genomes) - Cryptochlorogenic acid

http://www.ebi.ac.uk/ - Cryptochlorogenic acid

http://www.ncbi.nlm.nih.gov/ - Cryptochlorogenic acid

Journal of Chromatography
Chlorogenic acids can be easily converted into their respective regioisomers by means of a simple base-catalyzed intramolecular migration of the cinnamoyl group around the vicinal hydroxyls on the quinic acid moiety [24]. Reaction conditions, i.e. base nature, base-substrate concentration ratio and time, were optimized using 5-CQA as a general reference for the preparation of a total of nine CGAs from the coffee extract: 3-CQA (neochlorogenic acid), 4-CQA (cryptochlorogenic acid), 5-CQA, the three analogous feruloyl conjugates and three isochlorogenic acids 3,5-diCQA, 3,4-diCQA and 4,5-diCQA. Independent isomerization of the major CGAs present in coffee beans, once separated by CPC in a first step,was carried out then by treating an aqueous solution of 5-CQA, 5-FQA or 3,5-diCQA (30 mL, 10mg/mL) with sodium hydroxide (15mL, 1M) for 5 s while stirring. The mixture was immediately acidified by adding enough 6.0M HCl and desalted on a polyamide column eluted with water and acidic methanol. Evaporation under reduced pressure of the organic solvent yielded in all cases an almost equimolar isomeric mixture of the CGAs.

 

SALES SPECIFICATION

APPEARANCE

white crystalline powder

ASSAY

98.0% min

OPTICAL ROTATION

-71.0° ~ -81.0° (c=0.5 in H2O)

LOSS ON DRYING

3.0% max

HEAVY METALS

20ppm max

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

Not regulated

HAZARD CLASS

  
PACKING GROUP  

 

SAFETY INFORMATION

HAZARD OVERVIEW

May cause eye and skin irritation. May cause respiratory and digestive tract irritation. Target Organs: Not known.

HAZARD CODES

 

RISK PHRASES

 

SAFETY PHRASES

 24/25

 

PACKING

Preserve in light-resistant and well-closed containers