CAFFEIC ACID

PRODUCT IDENTIFICATION

CAS NO. 331-39-5

CAFFEIC ACID

EINECS NO. 206-361-2
FORMULA (HO)2C6H3CH=CHCOOH
MOL WT. 180.16

H.S. CODE

2918.29.2000

TOXICITY

 
SYNONYMS  3,4-Dihydroxycinnamic acid; trans-Caffeate; Caffeic acid;
3,4-Dihydroxy-trans-cinnamate; (E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid; 3,4-Dihydroxybenzeneacrylicacid; Cichoric acid; 3-(3,4-Dihydroxyphenyl)-2-propenoic acid; 4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene; 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene;
SMILES

c1(cc(c(cc1)O)O)/C=C/C(=O)O

CLASSIFICATION

Carbocyclic carboxylic acid,

EXTRA NOTES

Overall Carcinogenic Evaluation: Group 2B
A natural dietary phenolic compound found in plants that is an anti-oxidant. Inhibits the synthesis of leukotrienes that are involved in immunoregulation, inflammation and allergy. Inhibits Cu2+-induced LDL oxidation.

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE yellow crystals
MELTING POINT 222 - 225 C (Decomposes)
BOILING POINT  
SPECIFIC GRAVITY  
SOLUBILITY IN WATER soluble in hot water (soluble in alcohol)
pH  
VAPOR DENSITY

 

AUTOIGNITION

 

NFPA RATINGS Health: 2; Flammability: 0; Reactivity: 0

REFRACTIVE INDEX

 
FLASH POINT  
STABILITY

Stable under ordinary conditions

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

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

PubChem Compound Summary - Caffeic acid

IPCS INCHEM - Caffeic acid

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

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

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

Material Safety Data Sheet

http://toxnet.nlm.nih.gov/
Hazardous Substances Data Bank -
Caffeic acid

http://www.wisegeek.com/
Even though caffeic acid can be found in coffee, it is unrelated to caffeine. Together with its derivative caffeic acid phenethyl ester (CAPE), caffeic acid is a naturally occurring organic compound that is the product of many plants, including coffee beans. Caffeic acid is an antioxidant and it can also act as a carcinogenic inhibitor. Antioxidants, including caffeic acid, are essential in preventing diseases such as cancer or coronaries. Antioxidants consist of a molecule that is able to slow or even prevent oxidation of other molecules. When oxidation occurs in the body, it produces free radicals that are capable of damaging cells. Antioxidants terminate this reaction by removing free radicals that can be encouraged by smoking, stress, infections eating fried foods, excessive sunbathing, or exposure to pollution and x-rays. When the body has low levels of antioxidants, damage or death to cells can happen via a process called oxidative stress. This stress is a known contributor to the onset of many diseases, however it is not 100 percent understood whether it is the cause or the consequence of disease. The most common diseases are strokes and degenerative diseases. Caffeic acid also inhibits carcinogens. Carcinogens refer to any substances or agents that are involved in the promotion of cancer. There are any number of substances that can cause carcinogenic activity, but usually they are all related to the amount of radiation they emit.

Local:
Caffeic acid is a non-nitrogenous acid found in various plants as a metabolite product in nature. It is related to cinnamic acid. But it has two hydroxyl groups which is not found in cinnamic acid. Caffeic acid is not related to caffeine. Chlorogenic acid is the ester of caffeic acid with the 3-hydroxyl group of quinic acid. Caffeic acid is known as a naturally occuring phenolic acid which acts as a carcinogenic inhibitor. It is also known as an antioxidant in vitro and therefore contribute to the prevention of cardiovascular disease. Caffeic acid and its derivatives are used as a component of antimitogenic, anticarcinogenic, anti-inflamatory, and immunomodulator. In biological chemistry, cinnamic acid  is a key intermediate in shikimate and phenylpropanoid pathways. Shikimic acid is a precursor of many alkaloids, aromatic amino acids, and indole derivatives. Phenylpropanoid are a class of plant metabolites based on phenylalanine. They are widely distributed in plants fulfilling many functions including plant defense mechanism, pigmentation and external signaling system. Phenylalanine is first converted to cinnamates, coumarines, caffeic acids, ferulic acids, and sinapic acids. Cinnamic acid is the precursor of these acids. Cinnamic acid is the parent compound of its esters which are more volatile to be transported to other parts easily. Commercial cinnamic acid, a phenylacrylic acid structure compound, is used in converting to its esters such as methyl, ethyl, and benzyl cinnamate for the perfume and flavour application. Cinnamic acid and Its derivatives including esters and carboxylic functional derivatives are used as important components in flavours, perfumes, synthetic indigo and pharmaceuticals. Cinnamate can act as optical filters or deactivate substrate molecules that have been excited by light for the protection polymers and organic substances. They, cosmetic grades, are used as sunscreen agents to reduce skin damage by blocking UV-A, B. Cinnamic acid is an odorless white crystalline powder; slightly soluble in water; melting point 133 C and boiling point 300 C.

SALES SPECIFICATION

APPEARANCE

yellowish powder
ASSAY

98.5% min

LOSS ON DRYING

0.5% max

RESIDUE ON IGNITION

0.5% max

MELTING POINT 222 - 225 C
TRANSPORTATION
PACKING
 
HAZARD CLASS  
UN NO.

Not regulated

SAFETY INFORMATION

HAZARD OVERVIEW

Causes eye, skin, and respiratory tract irritation. Target Organs: Respiratory system, eyes, skin.

GHS

 

SIGNAL WORD Warning

PICTOGRAMS

HAZARD STATEMENTS

H315-H319-H335-H351-H361

P STATEMENTS

P261-P281-P305 + P351 + P338

EC DIRECTIVES

 

HAZARD CODES

RISK PHRASES

63-36/37/38-40-68

SAFETY PHRASES

26-36/37/39

PRICE INFORMATION