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    ????

    ????
    ???? ??? ???
    ?? ??:
    331-39-5
    ???:
    ????
    ???(??):
    ???;????;????;??????
    ???:
    Caffeic acid
    ???(??):
    Caffeic;31-39-5;NSC 623438;CAFFIC ACID;CAFFEIC ACID;AKOS B004050;Caffeic acid 0;cis-caffeicaci;Caffeicacid,96%;CaffeicAcidPure
    CBNumber:
    CB6281061
    ???:
    C9H8O4
    ??? ??:
    180.16
    MOL ??:
    331-39-5.mol

    ???? ??

    ???
    211-213 °C (dec.) (lit.)
    ?? ?
    272.96°C (rough estimate)
    ??
    1.2933 (rough estimate)
    ???
    1.4500 (estimate)
    ?? ??
    2-8°C
    ???
    ethanol: 50 mg/mL
    ?? ?? (pKa)
    4.58±0.10(Predicted)
    ??? ??
    powder
    ??
    yellow to tan
    ???
    soluble in hot water
    Merck
    14,1635
    BRN
    2210883
    ???
    Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
    InChIKey
    QAIPRVGONGVQAS-DUXPYHPUSA-N
    CAS ??????
    331-39-5(CAS DataBase Reference)
    IARC
    2B (Vol. 56) 1993
    NIST
    Cinnamic acid, 3,4-dihydroxy-(331-39-5)
    EPA
    2-Propenoic acid, 3-(3,4-dihydroxyphenyl)- (331-39-5)
    ??
    • ?? ? ?? ??
    • ?? ? ???? ?? (GHS)
    ??? ?? Xn,Xi
    ?? ???? ?? 36/37/38-40-63-68
    ????? 26-36/37/39-36
    WGK ?? 3
    RTECS ?? GD8950000
    ?? ?? ?? Irritant
    HS ?? 29182990
    ?? ?? ??? 331-39-5(Hazardous Substances Data)
    ????(GHS):
    ?? ?: Warning
    ??·?? ??:
    ?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
    H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? P264, P280, P302+P352, P321,P332+P313, P362
    H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? P264, P280, P305+P351+P338,P337+P313P
    H335 ?? ???? ??? ? ?? ?? ???? ?? - 1? ??;???? ?? ?? 3 ??
    H351 ?? ??? ??? ??? (????? ?? ???? ???? ???? ??? ?? ????? ??? ???? ??) ??? ?? ?? 2 ?? P201, P202, P281, P308+P313, P405,P501
    H361 ?? ?? ????? ??? ??? ??? ??? ???? ?? ?? 2 ?? P201, P202, P281, P308+P313, P405,P501
    ??????:
    P201 ?? ? ?? ???? ?????.
    P202 ?? ?? ?? ??? ?? ???? ??? ???? ???.
    P261 ??·?·??·???·??·...·????? ??? ????.
    P264 ?? ??? ?? ??? ????.
    P264 ?? ??? ?? ??? ????.
    P280 ????/???/???/?????? ?????.
    P281 ???? ?? ???? ?????
    P305+P351+P338 ?? ??? ? ?? ?? ???? ????. ???? ?????? ?????. ?? ????.
    P308+P313 ?? ?? ??? ???? ???? ??· ??? ????.
    P405 ???? ?????.
    P501 ...? ??? / ??? ?? ???.
    NFPA 704
    0
    2 0

    ???? MSDS


    Caffeic acid

    ???? C??? ??, ??, ??

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    Caffeic acid is abundant in the whole plant of Solidago decurrens Lour. (Yi Zhi Huang Hua), fruit of Crataegus pinnatifida Bge. var. major N.E.Br. (Shan Li Hong), Salix myrtillacea Anderss. (Po Liu), rhizome of Cimicifuga foetida L., rhizome of Polypodiaceae Polypodium vulgare L. (Ou Ya Shui Long Gu), peel of Rutaceae Citrus limonum (Ning Meng), the whole plant of Polygonaceae Polygonum aviculare L. (Pian Xu), root of Valeriana officinalis L. (Xie Cao), the whole plant of Thymus mongolicus Ronn (She Xiang), leaves of Eucommia ulmoides (Du Zhong), and other herbal plants. It is a kind of polyhydroxy styrene acid, with the general chemical properties of phenolic acid. It is easily oxidized for the reason of the unsaturated double bonds, particularly unstable in alkaline solution
    Caffeic acid has both cis and trans isomers, and the two isomers of caffeic acid have a mutual transformation in plants, which may regulate some important physiological process. Caffeic acid exists in plants in the main form of complexes; free state accounts for a few proportion.

    ??

    Caffeic acid is an inhibitor of 5-LO with an IC50 value of 3.7-72 μM and 12-LO with an IC50 value of 5.1-30 μM.

    ??? ??

    Light yellow to greenish-yellow powder

    ??? ??

    Appearance: yellow crystal. The crystal from the concentrated solution does not contain crystal water, and the crystal from the dilute solution contains one molecule crystal water. Melting point: 223?225?°C. Solubility: It is slightly soluble in cold
    water but soluble in hot water, cold ethanol, and ethyl acetate. The basic solution is orange-red. Ferric chloride solution was dark green.

    ??

    Caffeic acid has been used as a standard of phenolic acid in the study to determine the total phenolic acid content in vegetables after subjecting to alkaline and acid hydrolysis. It has also been used to determine its antioxidant activity by various assay methods.

    ??

    antineoplastic, PGE2 synthase inhibitor, PK inhibitor

    ??

    Caffeic Acid is a constituent of plants, probably occurs in plants only in conjugated forms. Caffeic acid is found in all plants because it is a key intermediate in the biosynthesis of lignin, one of the principal sources of biomass. Caffeic acid is one of the main natural phenols in argan oi.

    Indications

    It is used for preventing or stopping bleeding during surgery, as well as hemostasis in the department of medicine, obstetrics and gynecology, etc. It is also used for various causes of neutropenia and thrombocytopenia.

    ?? ??

    Yellow prisms or plates (from chloroform or ligroin) or pale yellow granules. Alkaline solutions turn from yellow to orange.

    ??? ?? ??

    Insoluble in water.

    ?? ???

    Caffeic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Caffeic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

    ????

    ACUTE/CHRONIC HAZARDS: When heated to decomposition Caffeic acid emits acrid smoke and fumes.

    ????

    Flash point data for Caffeic acid are not available; however, Caffeic acid is probably combustible.

    Biochem/physiol Actions

    A natural dietary phenolic compound found in plants that is an anti-oxidant. Inhibits the synthesis of leukotrienes that are involved in immunoregulation, inflammation and allergy. Inhibits Cu2+-induced LDL oxidation.

    Purification Methods

    Recrystallise this antioxidant from water. [Beilstein 10 IV 1776.]

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