6537-80-0

Basic information

• Product Name: ChicoricAcid
• Synonyms: Chicoric;(2R,3R)-2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic acid;(2R,3R)-2-O,3-O-Bis[3-(3,4-dihydroxyphenyl)acryloyl]tartaric acid;[2R,3R,(-)]-2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic acid;2-O,3-O-Bis[3-(3,4-dihydroxyphenyl)propenoyl]-L-tartaric acid;Chicoric acid;Butanedioic acid, 2,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (R-(R*,R*))-;Dicaffeoyltartaric acid CICHORIENSAURE
• CAS NO: 6537-80-0
• Molecular Formula: C₂₂H₁₈O₁₂
• Molecular Weight: 474.37
• Product Categories: Aromatic Phenols;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 6537-80-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 200～208℃
• Boiling Point: 785 °C at 760 mmHg
• Flash Point: 272.9 °C
• Appearance: /
• Density: 1.641g/cm³
• Vapor Pressure: 5.86E-26mmHg at 25°C
• Refractive Index: 1.726
• Storage Temp.: ?20°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly)
• PKA: 1.47±0.25(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: ChicoricAcid(CAS DataBase Reference)
• NIST Chemistry Reference: ChicoricAcid(6537-80-0)
• EPA Substance Registry System: ChicoricAcid(6537-80-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-42/43
• Safety Statements: 22-36/37-45
• WGK Germany: 3
• Hazardous Substances Data: 6537-80-0(Hazardous Substances Data)

Usage

Chicory extract

Cicory acid is a water-soluble phenolic acid compound extracted from the dry whole grass of the Compositae.It is anti-inflammatory, can enhance immune function and induce cell apoptosis. It can also inhibit hyaluronidase and protect collagen from the free radical that can be degraded.

Plant origin

Base source The dry roots, stems, leaves and flowers of the Compositae. Plant morphology Perennial herb, 40~120 cm high, with a gray whiteplant. The root is hypertrophy.Stems are erect, prismatic and hollow. The branches are skewed and ?thick at the apex with sparsely coarse hair or sericite and rarely no hair case.The basal leaves and the lower leaves of the stem split in the form ofupside pinniform down to the whole, 5~11 cm long and 1~2 cm wide. Apex lobes are larger and lateral lobes are triangular. Basal part is gradually narrowed into winged petioles; Stem leaves are sessile and the leaves gradually become smaller witha small number. Lanceolate ovate to lanceolate and the upper leaves are small. Below all the leaves are sparsely coarse hair or sericite. For the capitulum inflorescence single stem and branch end, 2~3 will cluster in the upper middle axillary fascicles; Involucre is cylindrical, 8~14 mm long; The outer layer of the involucre is of different shapes and lengths. The length of the length is different. The lower part feels like soft leather with lashes and hairy or non-hairy outside. All the flowers are ligulate and the Corolla is blue. The apex of the achenes is truncated and pappus is short, shaping like Scale and the apex is finely toothed. The flowering period is from July to August, and the fruit period is September. Habitat and distribution It grows in the foot of the mountain wetland, the beach barren hills and other places. It is produced in Shenyang, Dalian and other cities. Figure 1 Chicory

Stability

The effect of pH value on the stability of chicory acid The effects of different pH on the stability of chicory are different. The degradation rate of chicory acid in strong acid environment is lower than that in weak alkali environment. The effect of temperature on the stability The high temperature leads to the accelerated degradation of chicory acid, and the low temperature is beneficial to the stability of chicory. The effect of metal ions on the stability Na+ and K+ did not react with chicory acid; But the reaction of chicory with CaCl2 solution is very rapid, and the mechanism of yellowing of the solution remains to be further explored.The complexity of the food system leads to the mixing of various metal ions. Other metal ions, such as Ca2+, may have a great effect on chicory acid. When chicory acid is applied to food, we should consider the effect of metal ions on chicory acid in liquid food environment or in the post-flush environment so as to avoid the reaction resulting in the degradation of chicory acid and the changes of food quality. Effect of UV on the stability of chicory acid In methanol, chicory is more susceptible to ultraviolet light and isomerization into icricicory. The conversion rate of isomerization of chicory is higher because the polarity of methanol is smaller than that of water.When chicory is used in food, It should be taken into consideration that the sensitivity of chicory acidafter dissolving to ultraviolet light is higher. In the process, contact with ultraviolet light should be reduced. Study on its stability in fruit juice and beverage The low temperature storage is more favorable to the stability of chicory than the room temperature. At room temperature (25 ℃), cicory acid 15d will be completely decomposed in the water solution, indicating that the beverage system could protect cicory from degradation to some extent. The juice and beverage system itself is very complex. It is indicated that 100 mg vitamin C is added to the system of 445mL, which has antioxidant effect and can protect chicory to a certain extent. Therefore, the concentration of chicory is still at a high level even for 3 months. Study on its stability in milk powder Milk powder is a representative solid food environment. All the components in water activity is very small and ?relatively stable when isolated from air, water vapor and in light avoidance environment. This is for the lack of environmental factors that cause chicory acid degradation. Therefore, the concentration changes of chicory acid are not affected by the time and the milk powder system. In dry and room temperature storage, chicory can remain relatively stable in the milk powder system. Study on its stability in jelly The jelly system itself is very stable, and its water activity is very small. Chicory can be kept stable for a long time when it is stored under such a relatively closed condition, isolated from oxygen and water vapor.The slight fluctuations in the detection data may be caused by the error of the sample processing.

Uses

Different sources of media describe the Uses of 6537-80-0 differently. You can refer to the following data:
1. Chicoric Acid is an effective inhibitor of human immunodeficiency virus type-1 (HIV-1) integrase and the replication in tissues. Also a class of cannabinomimetics with CB2 receptor-dependent and indep endent
2. Chicoric Acid is an effective inhibitor of human immunodeficiency virus type-1 (HIV-1) integrase and the replication in tissues. Also a class of cannabinomimetics with CB2 receptor-dependent and independent

InChI:InChI=1/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m0/s1

Upstream product

• 6537-80-0 caftaric acid 
• 6537-80-0 (-)-chicoric acid 
• 203571-40-8 3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester 
• 331-39-5 caffeic acid 
• 82592-68-5 (E)-3,4-di-O-acetylcaffeoyl chloride 
• 204273-54-1 (2R,3R)-2,3-Bis-[(E)-3-(3,4-diacetoxy-phenyl)-acryloyloxy]-succinic acid di-tert-butyl ester 
• 54429-62-8 (E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid 
• 74257-25-3 ethyl caffeate 
• 488148-82-9 dibenzyl (-)-(2R,3R)-2,3-bis{3-[2,3-bis(3,4-dibenzyloxy)phenyl]prop-2-enoyloxy}-L-tartrate 
• 87-69-4 L-Tartaric acid 
• 488148-83-0 dibenzyl (+)-(2S,3S)-2,3-bis{3-[3,4-bis(benzyloxy)phenyl]prop-2-enoyloxy}-D-tartrate 
• 147-71-7 D-tartaric acid 

Downstream Products

• 6537-80-0 cis-chicoric acid 

Relevant articles and documents

A convenient synthesis of the Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (-)-(2R,3R)-chicoric acid

The Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (-)-chicoric acid (=2,3-bis{[3- (3,4-dihydroxyphenyl)-1-oxoprop-2-enyl]oxy}butanedioic acid; 1a) was conveniently prepared via a silane-promoted Pd-mediated chemoselective hydrogenolysis of its perbenzylated derivative 12a, which was generated from an efficient and reliable carbodiimide-mediated coupling reaction between the caffeic acid dibenzyl ether derivative 7 and commercially available (+)-dibenzyl L-tartrate (9a). The other naturally occurring dextrorotatory chicoric acid (1b) can be similarly prepared.