5-O-Caffeoylshikimic acid

Basic Information

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CAS Number

73263-62-4

Molecular Formula

C20H20O10

Molecular Weight

420.37 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Physical State

Powder

SMILES

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C1C(C(C(C=C1C(=O)O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O

InChI

InChI=1S/C20H20O10/c1-10(21)28-15-5-3-12(7-16(15)29-11(2)22)4-6-18(24)30-17-9-13(20(26)27)8-14(23)19(17)25/h3-8,14,17,19,23,25H,9H2,1-2H3,(H,26,27)/b6-4+/t14-,17-,19-/m1/s1

InChIKey

CVOWANZDPRDGEP-CDOWVBKTSA-N

LogP

0.5986999999999993

Topological Polar Surface Area

156.66 Å²

Hydrogen Bond Donor/Acceptor

3 / 10

Complexity

540

Synonyms & References

English

5-CSA
NCGC00180823-01
NCGC00180823-02!(3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxycyclohexene-1-carboxylic acid
5-(trans-caffeoyl)shikimic acid
TRANS-5-O-CAFFEOYLSHIKIMIC ACID
MEGxp0_000239
1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-p ropenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))-
CS-0143081
(3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxycyclohexene-1-carboxylic acid
5-caffeoylshikimic acid
MolPort-001-740-420
(3R,4R,5R)-5-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,4-dihydroxy-1-cyclohexene-1-carboxylic Acid
5U399BD0RZ
PD166603
Dactylifric acid
1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))-
(3R,4R,5R)-5-(((E)-3-(3,4-Dihydroxyphenyl)acryloyl)oxy)-3,4-dihydroxycyclohex-1-enecarboxylic acid
(3R,4R,5R)-5-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
UNII-5U399BD0RZ
DTXSID501312675
(3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxy-cyclohexene-1-carboxylic acid
E80649
Q27105553
5-O-Caffeoylshikimic acid
NCGC00180823-02
5-[(E)-caffeoyl]shikimic acid
TRANS-CAFFEIC ACID 5-O-SHIKIMATE
AC1NQZ12
73263-62-4
CHEBI:2106
AKOS040760230

MDL Number

MFCD22586495

FAQ

What are the physical and chemical properties of 5-O-Caffeoylshikimic acid (CAS: 73263-62-4)?

5-O-Caffeoylshikimic acid is a crystalline compound with a molecular weight of approximately 338.13 g/mol. It is slightly soluble in water and ethanol. Chemically, it is less reactive than many other phenolic compounds due to its conjugated structure. It is stable under normal conditions but can degrade when exposed to strong acids or bases.

How is 5-O-Caffeoylshikimic acid (CAS: 73263-62-4) typically synthesized?

5-O-Caffeoylshikimic acid is usually synthesized via a multi-step process starting from shikimic acid and caffeic acid. The synthesis involves esterification, followed by coupling reactions. Commonly used catalysts include sulfuric acid, and the overall yield is around 70-80%. The process requires careful control of temperature and pH to ensure high selectivity.

What industries use 5-O-Caffeoylshikimic acid (CAS: 73263-62-4)?

5-O-Caffeoylshikimic acid is used in the pharmaceutical industry for its antioxidant and anti-inflammatory properties. It also finds applications in the food industry as a natural food additive. Other industries that utilize this compound include the cosmetics industry for its potential skin care benefits and the research sector for its role in studying plant secondary metabolites.

What precautions should be taken when handling 5-O-Caffeoylshikimic acid (CAS: 73263-62-4)?

When handling 5-O-Caffeoylshikimic acid, it is important to use appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Work should be conducted in a fume hood due to its potential irritant properties. Spills should be cleaned up with a fume hood and the area should be well-ventilated. Always refer to the Safety Data Sheet (SDS) for detailed handling and storage instructions.