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trans-Chlorogenic acid

trans-Chlorogenic acid structure

CAS No:
202650-88-2
Formula:
C16H18O9
Chemical Name:
trans-Chlorogenic acid
Synonyms:
Cyclohexanecarboxylic acid,3-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4,5-trihydroxy-,(1S,3R,4R,5R)-;Cyclohexanecarboxylic acid,3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-,[1S-[1α,3β(E),4α,5α]]-;Cyclohexanecarboxylic acid,3-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-,(1S,3R,4R,5R)-;(1S,3R,4R,5R)-3-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid;trans-Chlorogenic acid;(-)-5-Caffeoyl quinic acid;trans-Caffeic acid 5-O-D-quinate;trans-3-O-Caffeoylquinic acid;5-O-(E)-Caffeoylquinic acid;5-trans-O-Caffeoylquinic acid;5-Ocaffeoylquinic acid

Description

Solid

Chlorogenic acid is a cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 3-hydroxy group of quinic acid. It is an intermediate metabolite in the biosynthesis of lignin. It has a role as a plant metabolite and a food component. It is a cinnamate ester and a tannin. It derives from a (-)-quinic acid and a trans-caffeic acid. It is a conjugate acid of a chlorogenate.|Chlorogenic Acid has been used in trials studying the treatment of Advanced Cancer and Impaired Glucose Tolerance.|Chlorogenic Acid is a polyphenol and the ester of caffeic acid and quinic acid that is found in coffee and black tea, with potential antioxidant and chemopreventive activities. Chlorogenic acid scavenges free radicals, which inhibits DNA damage and may protect against the induction of carcinogenesis. In addition, this agent may upregulate the expression of genes involved in the activation of the immune system and enhances activation and proliferation of cytotoxic T-lymphocytes, macrophages, and natural killer cells. Chlorogenic acid also inhibits the activity of matrix metalloproteinases.|A naturally occurring phenolic acid which is a carcinogenic inhibitor. It has also been shown to prevent paraquat-induced oxidative stress in rats. (From J Chromatogr A 1996;741(2):223-31; Biosci Biotechnol Biochem 1996;60(5):765-68).

trans-Chlorogenic acid Basic Attributes

Molecular Weight：

354.31 g/mol

Exact Mass：

354.31

EC Number：

206-325-6

UNII：

318ADP12RI

DSSTox ID：

DTXSID3024786

NCI Thesaurus Code：

C116073

Characteristics

PSA：

165 Å²

XLogP3：

-0.356 (est)

Melting Point：

205-209°C

Boiling Point：

664.95°C.@760.00mmHg(est)

Water Solubility：

0.11 M|40 mg/mL at 25 °C

Collision Cross Section：

185.1 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|173.79 Å² [M+Na-2H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

Drug Information

MeSH Entry Terms：

3 Caffeoylquinic Acid

Computed Properties

Molecular Weight:354.31
XLogP3:-0.4
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:5
Exact Mass:354.09508215
Monoisotopic Mass:354.09508215
Topological Polar Surface Area:165
Heavy Atom Count:25
Complexity:534
Defined Atom Stereocenter Count:4
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of trans-Chlorogenic acid

Description
Basic Attributes
Characteristics
Drug Information
Computed Properties
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