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ChemicalBook >> CAS DataBase List >>Chlorogenic acid

Chlorogenic acid

CAS No.
327-97-9
Chemical Name:
Chlorogenic acid
Synonyms
CAFFEOYLQUINIC ACID;Heriguard;3-CAFFEOYLQUINIC ACID;3-O-CAFFEOYLQUINIC ACID;Chlorogenic;ISOCHLOROGENIC ACID;CHLOROGENID ACID;CHLOROGENIC ACIDS;(1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxy-cyclohexane-1-carboxylic acid;Buthotoxin
CBNumber:
CB2478906
Molecular Formula:
C16H18O9
Molecular Weight:
354.31
MDL Number:
MFCD00003862
MOL File:
327-97-9.mol
MSDS File:
SDS
Last updated:2024-12-03 15:35:03

Chlorogenic acid Properties

Melting point 210 °C (dec.) (lit.)
Boiling point 407.55°C (rough estimate)
alpha -36 º (c=1, H2O)
Density 1.3594 (rough estimate)
refractive index -37 ° (C=1, H2O)
storage temp. 2-8°C
solubility Soluble in ethanol and acetone.
form Powder, Crystals, Needles and/or Chunks
pka 3.91±0.50(Predicted)
color White to almost white
Water Solubility SOLUBLE IN HOT WATER
Merck 14,2142
InChIKey CWVRJTMFETXNAD-JUHZACGLSA-N
LogP -0.356 (est)
CAS DataBase Reference 327-97-9(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 318ADP12RI
NCI Drug Dictionary chlorogenic acid
EPA Substance Registry System Chlorogenic acid (327-97-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xi
Risk Statements  68
Safety Statements  24/25
WGK Germany  3
RTECS  GU8480000
Hazard Note  Irritant
HS Code  29182900
Toxicity LDLo intraperitoneal in rat: 4gm/kg
NFPA 704
0
2 0

Chlorogenic acid price More Price(65)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHL89175 Chlorogenic acid phyproof? Reference Substance 327-97-9 50MG $322 2024-03-01 Buy
Sigma-Aldrich 1115545 Chlorogenic acid United States Pharmacopeia (USP) Reference Standard 327-97-9 50mg $394 2024-03-01 Buy
Sigma-Aldrich 00500590 Chlorogenic acid primary reference standard 327-97-9 25mg $520 2024-03-01 Buy
TCI Chemical C0181 Chlorogenic Acid Hydrate >98.0%(HPLC)(T) 327-97-9 1g $79 2024-03-01 Buy
TCI Chemical C0181 Chlorogenic Acid Hydrate >98.0%(HPLC)(T) 327-97-9 5g $276 2024-03-01 Buy
Product number Packaging Price Buy
PHL89175 50MG $322 Buy
1115545 50mg $394 Buy
00500590 25mg $520 Buy
C0181 1g $79 Buy
C0181 5g $276 Buy

Chlorogenic acid Chemical Properties,Uses,Production

Pharmacological action

Chlorogenic acid as the condensation product of caffeic acid and quinic acid, is blue when meeting with iron, which is similar to tannins , but not precipitated with protein, so no convergence. Caffeic acid and chlorogenic acid has the wide bacteriostasis, but can be inactivated protein in the body. This product is similar to caffeine, oral or intraperitoneal injection, can improve the rat central excitability. Oral the drug of chlorogenic acid and coffee acid can increase the amount of hydrochloric acid secretion in the stomach, and can make slow pulse, and quinic acid is not. Chlorogenic acid could significantly increase small intestine peristalsis on the rat or mouse. Chlorogenic acid, caffeic acid and quinic acid can increase the tension of rat uterus, this function can be cancelled by papaverine, while atropine can't influence. Caffeic acid, chlorogenic acid, also can promote bile secretion in rats. On the specimens of rabbit ileum in vitro, this product can enhance the effect of adrenaline, but has no effect on blood glucose of adrenaline.

Protecting liver, gallbladder

Chlorogenic acid in flos lonicerae has favorable gallbladder function, promoting biliary Secretion of rats. Injection of 200 mg/kg chlorogenic acid to browns MAO honeysuckle total saponins subcutaneous can be significantly against CCl4, paracetamol and the increase of serum GPT caused by galactosamine in mice liver and liver triglyceride levels, and significantly reduce the severity of the liver pathological damage, making dot necrosis number sum and necrosis occur rate liver decreased obviously.

The inhibitory effect on hyaluronidase and glucose - 6 - phosphatase

Hyaluronic cranberry (HAase) is one of the cracking mucopolysaccharide enzymes, can catalyze hyaluronic acid (HA) decomposition,which is in relation to the permeability of vascular system and inflammation. HA is a mucopolysaccharide, which is composed of uronic acid and acetyl glucosamine, having a variety of functions, such as heal, make the skin wetting health, lubricating joints and prevent inflammation, etc. 3, 5-2 coffee acyl quinic acid (artichoke acid) and chlorogenic acid found in the ethyl acetate extract from the narrow assists cone flower (Echinacea amgustifolia DC) roots have stronger inhibitory effect of HAase activated. Animal in vitro studies have demonstrated that chlorogenic acid can not reversible inhibition of glucose-6-hydrolysis of phosphatase, reduce liver glycogen decomposition and exogenous glucose absorption. Animal studies have shown that the use of chlorogenic acid can reduce high blood sugar spikes caused by the use of glucagon (glycogenolysis). Therefore, chlorogenic acid can lower blood sugar level, improve the liver glucose-6-phosphoric acid and the concentration of hepatic glycogen.

The character of molecular structure

Chlorogenic acid is formed by caffeic acid and quinic acid, and the molecular structure has ester bond, unsaturated double bond and polyphenol unstable part of the three. In the process of extracted from plants, chlorogenic acid often happen by hydrolysis and intramolecular ester base migration isomerization . Due to the special structure of chlorogenic acid, it can extract from plants by the polarity solvent such as ethanol, acetone, methanol. But due to the instability of chlorogenic acid itself, extraction can not be in high temperature, strong light and heat for a long time. Chlorogenic acid liquid were placed in brown bottle, refrigerator (2 ℃) to save to be the most stable.

Preparation method

Chlorogenic acid can be obtained by (1S)-1-ethoxyformyloxy-3-cis-[3,4-dihydroxy-anti-cinnamoyl oxygen radicals]-4'-anti-5'-anti-dihydroxy cyclohexane-γ-methyl formate with barium hydroxide in methanol catalytic hydrolysis, or by the segregation from green coffee beans.

HPLC method for determination the content

(1)Chromatographic conditions: octadecyl silane bonded silica gel as the filling agent; Acetonitrile-0.4% phosphoric acid solution (13:87) as mobile phase; Detection wavelength of 327 nm. Theoretical plate number according to the chromatographic peak of chlorogenic acid is greater than 1000. (2)the preparation of the reference substance solution: precisely weigh the right amount of chlorogenic acid reference substance, placed in brown volumetric flask, adding 50% methanol solution containing 40 μg /mL (saving below 10 ℃). (3)the preparation of sample solution: taking samples of dry powder is about 0.5 g, precision said, with a plug in the conical flask, adding 50 ml 50% methanol , 30 min ultrasonic processing , cooling, weighing, make up the weight loss reduction with 50% methanol, shake well, filtration, abandoned the early filtrate, precision measuring duration of filtrate 5 ml, 25 ml volumetric brown flask , add 50% methanol to the scale, shake well. (4)assimilate precision respectively from each 10 μL reference substance and the sample solution, injection liquid chromatograph, determination,obtained.

Toxicity

Chlorogenic acid is sensitive to people, can cause asthma, dermatitis, but no this reaction to the oral of chlorogenic acid. It can be active no sensitization substances by small intestinal secretions convertion to. The toxicity of chlorogenic acid is very small, LD50 is greater than 1 g/kg to young rats, intraperitoneal injection of greater than 0.25 g/kg.

Chemical property

Hemihydrate is needle crystal (water). When 110 ℃, it become to anhydrous compounds. Melting point: 208 ℃, [alpha] 20D-35.2 (C = 2.8). When 25 ℃, water solubility was 4%, solubility is bigger in the hot water. Soluble in ethanol and acetone, slightly soluble in ethyl acetate.

Uses

It has broad antibacterial effect, advantageous bravery, hemostatic, increase white blood cell and antiviral effect, the effect of the blood clotting and bleeding time is shortened. It is used in the treatment of upper respiratory tract infection, anti-inflammatory and antipyretic, cool blood heat dissipation. Used as pharmaceutical raw materials and intermediates. clearing heat and removing toxicity, cold wind heat, broad-spectrum antimicrobial properties, having obvious inhibitory effect to hemolytic streptococcus, dysentery rod gas and salmonella typhi bacteria

Toxicity grading

toxication

Acute toxicity

Abdominal cavity-rat LDL0:4000 mg/kg

Flammability hazard characteristics

Combustible; Release acrid smoke fire

Storage and transport properties

Low temperature warehouse, ventilated, dry

Fire extinguishing agent

Water, carbon dioxide, dry powder, sand

Chemical Properties

white to slightly yellowish-beige powder

Uses

Chlorogenic acid is used as a food additive in coffee products, chewing gum and mint. It acts as an intermediate in the biosynthesis of lignin, which is an antioxidant.

Definition

ChEBI: 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 is functionally related to a (-)-quinic acid and a trans-caffeic acid. It is a conjugate acid of a chlorogenate.

General Description

Chlorogenic acid is a bioactive polyphenolic compound mainly found in many plants, such as coffee. It is a potent neuroprotectant and also possesses antiviral, antifungal, antioxidant and antitumor properties. CGA may also be involved in regulating glucose and lipid metabolism and improving insulin sensitivity.

Purification Methods

Crystallise the acid from water and dry it at 110o. [Beilstein 10 H 537, 10 I 271, 10 II 378, 10 III 2408, 10 IV 2259.]

Chlorogenic acid Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 727)Suppliers
Supplier Tel Email Country ProdList Advantage
Jiurui Biology Chemistry Co.,Ltd.
+86-0744-8561603 +8619974416182 sales11@jiuruibiochem.com China 26 58
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+86-0731-84213302 +86-18374838656 info@staherb.cn China 1025 58
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+8615373025980 clara@hbshengyang.com China 874 58
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View Lastest Price from Chlorogenic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Chlorogenic Acid pictures 2024-12-06 Chlorogenic Acid
327-97-9
 US $15.00 / kg 1kg 99% 5000kg/Week Hebei Zhuanglai Chemical Trading Co.,Ltd
Chlorogenic acid pictures 2024-12-06 Chlorogenic acid
327-97-9
 US $7.00 / KG 1KG 99% 20TONS Hebei Longbang Technology Co., Ltd
Chlorogenic acid pictures 2024-12-06 Chlorogenic acid
327-97-9
 US $6.00 / kg 1kg 99% 2000KG/Month HebeiShuoshengImportandExportco.,Ltd
  • Chlorogenic Acid pictures
  • Chlorogenic Acid
    327-97-9
  • US $15.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co.,Ltd
Chlorogenic acid, 98%, predoMinantly trans, froM coffee seeds Igasuric acid Chlorogenic acid ( green coffe bean extract) Chlorogenil acid Chlorogenic ac Chlorogenic acid Synonyms green coffe bean extract Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4,5-trihydroxy-, (1S,3R,4R,5R)- Chlorogenic acid (1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid Chlorogenic acid (98%HPLC) Chlorogenic acid >=95% (titration) 3-CAFFEOLYQUINICACID Chlorogenic Acid Hydrate Chlorogenic acid, 99%, predominantly trans, from coffee seeds [1S,4R,5R,(-)]-3β-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid 1,4α,5α-Trihydroxy-3β-[3-(3,4-dihydroxyphenyl)acryloyloxy]cyclohexane-1β-carboxylic acid Honegsukle Flowers Extract 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate) 3-(3,4-Dihydroxycinnamoyl)quinic Acid CHLOROGENIC ACID extrapure Chlorogenic acid，3-Caffeoylquinic acid Chlorogenic Acid (50 mg) Chlorogenic Acid (50 mg)F0C4200.97mg/mg(ai) Buthus martensii Karsch .p.e Chlorogenic acid ,98% Chlorogenic acid (Honeysuckle Flower P.E.) Chlorogenic acid (froM EucoMMia Bark) Eucommia Leaf Extract-- chlorogenic acid eucommin leaf extract 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate) 3-(3,4-Dihydroxycinnamoyl)quinic Acid 3-O-Caffeoylquinic acid CHLOROGENIC ACID, TRANS CHLOROGENIC ACID HELIANTHIC ACID CAFFEOLYQUINIC ACID CAFFETANNIC ACID CAFFEYLQUINIC ACID (1s,3r,4r,5r)-3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid 3-[[3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL]OXY] 1,4,5-TRIHYDROXYCYCLOHEXANECARBOXYLIC ACID 3-(3,4-DIHYDROXYCINNAMOYL)-D(-)-QUINIC ACID 3-(3,4-DIHYDROXYCINNAMOYL)QUINIC ACID 1,3,4,5-TETRAHYDROXY-CYCLOHEXANECARBOXYLIC ACID 3-[3,4-DIHYDROXYCINNAMATE] 5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid 5-(3,4-DIHYDROXYCINNAMOYL)-D-(-)-QUINIC ACID 3R-[[3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL]OXYL]-1S,4R,5R-TRIHYROXY-CYCLOHEXANECARBOXYLIC ACID 3-O-(3,4-DIHYDROXYCINNAMOYL)-D-QUINIC ACID NSC 407296 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-cyclohexanecarboxylicaci Chlorogenic acid, predominantly trans, from coffee seeds, 99% Cyclohexanecarboxylic acid, 3-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyloxy-1,4,5-trihydroxy-, (1S,3R,4R,5R)- chlorogenic acid (natural) CHLOROGENIC ACID PLANT CELLCULTURE TESTE D CHLOROGENIC ACID CRYSTALLINE CHLOROGENIC ACID, PREDOMINANTLY TRANS ChlorogenicAcid(EucommiaUlmoidesOliverPe)20%ByHplc 3-[3-C[3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENY1]OXY]1,4,5-TRIHYDROXY-,[1S-(1α,3β,4α,5α)]- 5-trihydroxy-,(1s-(1-alpha,3-beta,4-alpha,5-alpha))-4 CYCOLOHEXANECABOXYLIOACID Chlorogenic acid (froM Flos lonicerae) NSC 70861 (1S,3R,4R,5R)-3-[(E)-3-(3,4-DIHYDROXY-PHENYL)-ACRYLOYLOXY]-1,4, 5-TRIHYDROXYCYCLOHEXANECARBOXYLIC ACID