4,5-Dicaffeoylquinic acid

Basic Information

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CAS Number

57378-72-0

Molecular Formula

C25H24O12

Molecular Weight

516.46 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

Melting Point

140°C

Boiling Point

810.8℃ at 760 mmHg

Solubility

DMSO,Methanol,Acetontrile

SMILES

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C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O

InChI

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

InChIKey

UFCLZKMFXSILNL-RVXRWRFUSA-N

LogP

1.0295999999999996

Topological Polar Surface Area

211.27999999999997 Å²

Hydrogen Bond Donor/Acceptor

7 / 12

Complexity

887

Safety Information

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Storage Conditions

-20℃

Synonyms & References

English

(1R,3R,4S,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxy-cyclohexanecarboxylic acid
3,4-DCQA
NCGC00180681-01
(1R,3R,4S,5R)-3,4-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,5-dihydroxycyclohexanecarboxylic acid
Isochlorogenic acid C
57378-72-0
UNII-E57A0DKE0B
E57A0DKE0B
AS-74958
CCG-269823
BDBM50056908
MFCD10566623
isochlorogenic-acid-c
3,4-Di-O-Caffeoylquinic acid
NCGC00180681-03
Isochlorogenic acid C(4,5)
(1R,3R,4S,5R)-3,4-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,5-dihydroxycyclohexanecarboxylicacid
89886-30-6
Q27276885
CHEMBL177126
Cyclohexanecarboxylic acid, 3,4-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,5-dihydroxy-, (1R,3R,4S,5R)-
Isochlorogenic acid b
s9034
4,5-Dicaffeoylquinic acids
HY-N0058
4,5-Di-O-caffeoylquinic acid
ACon1_000313
Cyclohexanecarboxylic acid,3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,5-dihydroxy-,(1R,3R,4S,5R)-
3,4-Bis[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,5-dihydroxycyclohexanecarboxylic acid
4,5-Di-O-caffeoylquinic acid, >=85% (LC/MS-ELSD)
(1R,3R,4S,5R)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid

MDL Number

MFCD10566623

FAQ

What are the physical and chemical properties of 4,5-Dicaffeoylquinic acid (CAS: 57378-72-0)?

4,5-Dicaffeoylquinic acid is a crystalline compound with a molecular weight of approximately 508.17 g/mol. It has a low solubility in water but is more soluble in ethanol and methanol. Chemically, it is relatively stable but can undergo hydrolysis under alkaline conditions. This compound shows moderate reactivity towards acid-catalyzed cleavage and is sensitive to strong acids and bases.

How is 4,5-Dicaffeoylquinic acid (CAS: 57378-72-0) typically synthesized?

4,5-Dicaffeoylquinic acid is typically synthesized through the esterification of quinic acid with 4,5-dicaffeoyl-CoA, catalyzed by lipases. The synthesis involves a multi-step process including esterification, purification, and crystallization. The yield is generally around 70-80%, and the method provides good selectivity for the desired product.

What industries use 4,5-Dicaffeoylquinic acid (CAS: 57378-72-0)?

4,5-Dicaffeoylquinic acid finds applications in the pharmaceutical industry for its potential anti-inflammatory and antioxidant properties. It is also used in the food industry as a natural preservative and flavor enhancer. Additionally, it has applications in the cosmetic industry due to its potential skin-protecting effects and in the polymer industry for its antioxidant properties.

What precautions should be taken when handling 4,5-Dicaffeoylquinic acid (CAS: 57378-72-0)?

When handling 4,5-Dicaffeoylquinic acid, it is important to use appropriate personal protective equipment (PPE), including gloves and lab coats, to prevent skin contact. Store it in a cool, dry place, away from direct sunlight and heat sources. Use a fume hood during handling to minimize inhalation risk. In case of a spill, immediately clean up the area and consult the safety data sheet (SDS) for proper disposal procedures.