(1S,3R,4R,5R)-3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

• ChemBase ID: 72930
• Molecular Formular: C16H18O9
• Molecular Mass: 354.30872
• Monoisotopic Mass: 354.09508216
• SMILES: C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/c1cc(c(cc1)O)O)O)O
• Canonical SMILES: O=C(O[C@@H]1C[C@@](O)(C[C@H]([C@H]1O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1
• InChIKey: CWVRJTMFETXNAD-JUHZACGLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,4R,5R)-3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid; (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• IUPAC Traditional name: chlorogenic acid
• Synonyms: (1S,3R,4R,5R)-3-(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid; 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate); Chlorogenic acid; Chlorogenic acid; 3-(3,4-Dihydroxycinnamoyl)quinate; 3-(3,4-Dihydroxycinnamoyl)quinic acid; 3-Caffeoylquinate; 3-Caffeoylquinic acid; 3-CQA; 3-O-Caffeoylquinic acid; Chlorogenate; Chlorogenic acid; Heriguard; 3-trans-Caffeoylquinic acid; 1,3,4,5-四羟基环己烷羧酸 3-(3,4-二羟基肉桂酸酯); 3-(3,4-二羟基肉桂酰基)奎宁酸; 绿原酸

Database IDs

• CAS Number: 327-97-9
• EC Number: 206-325-6
• MDL Number: MFCD00003862
• PubChem SID: 24892649; 162037850
• PubChem CID: 1794427
• CHEBI ID: 16112
• CHEMBL: 284616
• Chemspider ID: 1405788
• Wikipedia Title: Chlorogenic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.3338532
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -2.4192955
• LogD (pH = 7.4): -3.6938899
• Log P: -0.26852977
• Molar Refractivity: 83.2347 cm^3
• Polarizability: 32.441044 Å^3
• Polar Surface Area: 164.75 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble, clear to hazy
• Apperance: crystalline; Powder
• Melting Point: 207 - 209°C; 208-210°C; 210 °C (dec.)(lit.)
• Density: 1.28 g/cm^3
• Optical Rotation: [α]25/D -35°, c = 2.8 in H2O

Safety Information

• Storage Condition: -20°C
• RTECS: GU8480000
• German water hazard class: 3
• Risk Statements: -
• Safety Statements: S24 S25 S28 S37 S45
• NFPA704:
  

  0

  1
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: rat ... G6pc(25634)

Product Information

• Purity: ≥95% (titration); 95+%
• Grade: primary reference standard
• Salt Data: Free Base
• Suitability: plant cell culture tested
• Empirical Formula (Hill Notation): C16H18O9

DETAILS

MP Biomedicals - 05202172

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2280

Research Area: Cardiovascular Disease , Immunology
Biological Activity:
Chlorogenic acid is a hydroxycinnamic acid and a member of a family of naturally occurring organic compounds. [1] These are esters of polyphenolic caffeic acid and cyclitol (-)-quinic acid. It is an important biosynthetic intermediate. It also is one of the phenols found in coffee, bamboo Phyllostachys edulis, as well as many other plants. This compound, long known as an antioxidant, also slows the release of glucose into the bloodstream after a meal. [2]

Sigma Aldrich - C3878

Caution
May yield a hazy solution in ethanol
Packaging
1, 5 g in poly bottle
250 mg in poly bottle

Sigma Aldrich - 00500590

Application
Reference standard in the analysis of herbal medicinal products
General description
Produced and qualified by HWI AnalytikExact content by quantitative NMR can be found on the certificate

REFERENCES

• ohnston KL et al. Am J Clin Nutr. 2003 Oct;78(4):728-33.