331-39-5 Usage
Physical and Chemical Properties
Caffeic acid, scientific name: "3-(3,4-dihydroxyphenyl)-2-propenoic acid." Molecular formula: C9H8O4; the molecular weight: 180.16. It is presented in plants such as coffee in the form of chlorogenic acid. It is yellow crystals with melting point being 223~225 °C. When it is precipitated in concentrated solution, it contains no crystal water. However, precipitate of crystals from dilute solution contains one molecule of crystallized water. It is slightly soluble in water, and easily soluble in hot water, cold ethanol, and ethyl acetate. Its alkaline solution is orange and exhibits dark green when being mixed with ferric chloride.
Application: caffeic acid is safe to be applied in cosmetics and has a broader antibacterial and antiviral activity. It can also absorb ultraviolet radiation. A low concentration of it already has inhibitory efficacy on the generation of skin melanin. Its applied amount in the beauty products for whitening is at the range of 0.5 to 2%. It can also be used as additive for the oxidized hair dyes which is good for enhancing the strength of the color.
Preparation: it can be produced from the Perkin’s reaction between protocatechuic aldehyde and acetic acid,As follows:
Extraction Method
Caffeic acid belongs to common phenolic compounds with effects of increasing the levels of white blood cells. It is easily to be confused with caffeine and is widely distributed in the plant kingdom. Its major plant sources include lemon peel, Ranunculaceae cimicifuga rhizome, and valerian root. Caffeic acid, together with ferulic acid, erucic acid, and p-hydroxy cinnamic acid are ubiquitous hydroxy cinnamic acid-class molecule distributed in various kinds of plants. This kind of products has conjugated double bonds in the side chain of the molecular structure, and thus exhibiting significant fluorescence upon ultraviolet light, mostly showing bluish color fluorescence. This is a advantage for paper chromatography tests or thin layer chromatography tests.
Extraction Method: Single spike cimicifuga rhizome is extracted with methanol which is removed through concentration under reduced pressure. Add hot water to the residue to dissolve it. Heating the water to dissolve the residue, and further filter the insolubles upon heating. After cooling, add benzene for extraction with the benzene solution being washed with 1% aqueous sodium bicarbonate and further collecting the washed solution. Add dilute hydrochloric acid for acidification, and then apply benzene to remove the free organic acid; Concentrate under reduced pressure to get rid of the benzene with the residue being the enriched product of caffeic acid.
The above information is edited by the lookchem of Dai Xiongfeng.
Drugs for white blood cells increase
Caffeic acid is a kind of drugs for stopping bleeding as well as increasing the number of white blood cell with effects of contracting microvascular coagulation, improving the function of coagulation factors, and increasing white blood cells and platelets. It is suitable for preventing bleeding or stopping bleeding in surgeries as well as for stopping bleeding for bleeding diseases in internal medicine, and obstetrics and gynecology. It is also suitable for treating leukopenia and thrombocytopenia caused by a variety of reasons.
HPLC determination of caffeic acid in dandelion
[For the test] Compositae dandelion: Taraxacum mongolicum Hand. Mazz, Alkali land dandelion T. sinicum Kitag.
(1) Chromatographic conditions: take octadecylsilane silica gel as a filling agent; methanol-phosphate buffer (sodium dihydrogen phosphate 1.56g, add water to dissolve it in 1000 ml, add 1% of phosphoric acid solution for adjusting to pH 3.8 to 4.0, that’s it) (23:77) as the mobile phase; detection wavelength is 323 nm; column temperature should be 40 °C. Number of theoretical plates should be calculated according to the caffeic acid peak and should not be less than 3,000.
(2) the preparation of the reference solution: take 7.5 mg of caffeic acid reference substance, accurately weigh it and transfer it into the 50ml volumetric flask; add methanol to certain scale, shake; take precise amount of 2ml and put into 10ml volumetric flask, add methanol to the scale , shake, to obtain the reference solution (containing caffeic acid 30μg per ml).
(3) Preparation of sample solution: Take about 1 g of medicine powder, accurately weigh it, and put it in 50ml Erlenmeyer flask, precisely add 10 mL of methanol solution containing 5% formic acid, seal, shake, weigh, and subject to ultrasonic treatment for 30min, remove, cool, then weigh again; use the methanol solution of 5% formic acid to complement the weight loss, shake, centrifuge, and take the supernatant for being filtrated through microporous membrane (0.45μm) with the filtrate being placed in brown bottle to obtain the sample solution.
(4) Determination: separately and precisely pipette 10μl of both reference solution and sample solution and transfer into the liquid chromatography for measurement.
(5) Measurement results: calculated from the dry products of dandelion herbs, the caffeic acid content should not be less than 0.02%.
Chemical Properties
Different sources of media describe the Chemical Properties of 331-39-5 differently. You can refer to the following data:
1. It is yellow crystals and can be dissolved in water and ethanol.
2. Light yellow to greenish-yellow powder
Uses
Different sources of media describe the Uses of 331-39-5 differently. You can refer to the following data:
1. 1. Reagents for Organic Synthesis.
2. Intermediate of caffeic acid; can be used in organic synthesis.
3. Used for Biochemical studies.
2. 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.
3. antineoplastic, PGE2 synthase inhibitor, PK inhibitor
4. 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.
Category
Toxic Chemicals
Toxicity grading
Poisoning
Acute toxicity
Intraperitoneal administration-rat LDL0: 1500 mg/kg
Flammability and hazard characteristics
Thermal decomposition causes irritating smoke
Storage Characteristics
Treasury: ventilation low-temperature and dry.
Extinguishing agent
Water, powder, CO2, foam.
Description
Different sources of media describe the Description of 331-39-5 differently. You can refer to the following data:
1. 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 solutionCaffeic 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.
2. 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.
Physical properties
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 coldwater but soluble in hot water, cold ethanol, and ethyl acetate. The basic solution is
orange-red. Ferric chloride solution was dark green.
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.
General Description
Yellow prisms or plates (from chloroform or ligroin) or pale yellow granules. Alkaline solutions turn from yellow to orange.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
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.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition Caffeic acid emits acrid smoke and fumes.
Fire Hazard
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 331-39-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,3 and 1 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 331-39:
(5*3)+(4*3)+(3*1)+(2*3)+(1*9)=45
45 % 10 = 5
So 331-39-5 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/p-1/b4-2+
331-39-5Relevant articles and documents
Ladroside (=6'-Caffeoyl-mussaenoside), a New Iridoid Glucoside from Veronica officinalis L. (Scrophulariaceae) and the Elucidation of the Absolute Configuration at C(8) of Mussaenoside
Affifi-Yazar, Fatma Ue.,Sticher, Otto,Uesato, Shinichi,Nagajima, Kimiko,Inouye, Hiroyuki
, p. 16 - 24 (1981)
A new iridoid glucoside, named ladroside, together with mussaenoside (1) , has been isolated from Veronica officialis L.The structure of ladroside (4) and the identity of mussaenoside have been established by spectral analysis.Additionally, the absolute configuration at C(8) carrying hydroxyl group has been established by chemical evidence.
MALONATED FLAVONOL GLYCOSIDES AND 3,5-DICAFFEOYLQUINIC ACID FROM PEARS
Wald, Burkard,Wray, Victor,Galensa, Rudolf,Herrmann, Karl
, p. 663 - 664 (1989)
Key Word Index--Pyrus communis; Rosaceae; pears; malonated flavonol glucosides; 3,5-dicaffeoylquinic acid.Abstract--3-O-(6''-O-malonyl)-β-Glucosides of quercetin, kaempferol, isorhamnetin and 3,5-dicaffeoylquinic acid were isolated and identified from leaves of pears.The compounds are also present in the fruits.
Two new monoterpenes and one dicaffeic acid ester from Sibiraea angustata with hypolipidemic activities in HepG2 cells in Vitro
Li, Bin,Chen, Xiaotian,Wang, Zhangwei,Liu, Hongdong,Liu, Bo,Yu, Shishan,Lai, Xuewen,Xu, Xianghong,Hayashi, Toshimitsu
, p. 319 - 323 (2015)
Two new monoterpenes, named sibiscolacton B (1) and sibiscolacton C (2), together with a sorbate obtained from the natural product 1, 6-sorbitol-O-dicaffeic acid ester (3), were isolated from an aqueous extract of the aerial portion of Sibiraea angustata. The compounds' structures were elucidated on the basis of extensive spectroscopic analysis, as well as literature comparisons. A preliminary in vitro bioassay showed that all of the compounds exhibited hypolipidemic effects in HepG2 cells.
Rhamnetin Glycosides from the Genus Spiraea
Olennikov,Chirikova
, p. 41 - 45 (2018)
Rhamnetin (7-O-methylquercetin,1) and its glycosides were found for the first time in the genus Spiraea (Rosaceae) during chromatographic studies of representatives from the subgenus Protospiraea. Leaves of S. salicifolia yielded1, rhamnetin-3-O-β-D-glucopyranoside (2), and two new flavonoids3and4that were identified by UV, IR, and NMR spectroscopy and mass spectrometry as rhamnetin-3-O-(6″-O-p-coumaroyl)-β-D-glucopyranoside (spiraearhamnin A,3) and rhamnetin-3-O-(6″-O-caffeoyl)-β-D-glucopyranoside (spiraearhamnin B,4). Leaves of S. betulifolia and S. betulifolia var. aemiliana afforded1and2and glycosides of kaempferol, quercetin, and isorhamnetin. Species of the subgenus Metaspiraea (S. alpina, S. chamaedryfolia, S. dahurica, S. hypericifolia, and S. media) did not contain1or its derivatives.
Cizmarik,Matel
, p. 713 (1970)
New thiophene and flavonoid from tagetes minuta leaves growing in saudi arabia
Al-Musayeib, Nawal M.,Mohamed, Gamal A.,Ibrahim, Sabrin R. M.,Ross, Samir A.
, p. 2819 - 2828 (2014)
Phytochemical investigation of the methanolic extract of Tagetes minuta L. (Asteraceae) leaves resulted in the isolation and identification of two new compounds: 5-methyl-2,2',5',2'',5'',2''',5''',2''''-quinquethiophene (1) and quercetagetin-6-O-(6-Ocaffe
Cytotoxic triterpenoid saponins from Clematis tangutica
Zhao, Min,Da-Wa, Zhuo-Ma,Guo, Da-Le,Fang, Dong-Mei,Chen, Xiao-Zhen,Xu, Hong-Xi,Gu, Yu-Cheng,Xia, Bing,Chen, Lei,Ding, Li-Sheng,Zhou, Yan
, p. 228 - 237 (2016)
Eight previously undescribed oleanane-type triterpenoid saponins, clematangoticosides A-H, together with eight known saponins, were isolated from the whole plants of Clematis tangutica (Maxim.) Korsh. Their structures were elucidated by extensive spectroscopic analysis, in combination with chemical methods (acid hydrolysis and mild alkaline hydrolysis). Clematangoticosides D-G were found to be unusual 23, 28-bidesmosidic glycosides. The cytotoxic activities of all of the isolated saponins were evaluated against the four human cancer cell lines SGC-7901, HepG2, HL-60 and U251MG. Clematoside S, sapindoside B, kalopanax saponin A, and koelreuteria saponin A exhibited cytotoxicity against all of the test cancer cell lines with IC50 values in the range of 1.88–27.20?μM, while clematangoticoside D and F showed selective cytotoxicity against SGC-7901 with IC50 values of 24.22 and 21.35?μM, respectively.
A new isoflavone from Blepharis ciliaris of an Egyptian origin
El-Shanawany, Mohamed A.,Sayed, Hanaa M.,Ibrahim, Sabrin R. M.,Fayed, Marwa A. A.,Radwan, Mohamed M.,Ross, Samir A.
, p. 2346 - 2350 (2013)
A phytochemical study of the aerial parts of Blepharis ciliaris (L.) B.L. Burtt. led to the isolation of one new isoflavone glycoside caffeic acid ester: genistein-7-O-(6″-O-E-caffeoyl-β-d-glucopyranoside) (4), along with seven known compounds: methyl veratrate (1), methyl vanillate (2), protocatechuic acid (3), naringenin-7-O-(3″-acetyl-6″-E-p-coumaroyl- β-d-glucopyranoside) (5), naringenin-7-O-(6″-E-p-coumaroyl-β-d- glucopyranoside) (6), apigenin-7-O-(6″-E-p-coumaroyl-β-d- glucopyranoside) (7), and acteoside (8). Their structures were established on the basis of detailed analyses of physical, chemical, and spectral data. Compounds 1, 2, 3, 6, and 8 were isolated for the first time from this plant. The antioxidant activity of the different extracts as well as for some of the isolated compounds was evaluated.
Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa1
Morikawa, Toshio,Pan, Yingni,Ninomiya, Kiyofumi,Imura, Katsuya,Matsuda, Hisashi,Yoshikawa, Masayuki,Yuan, Dan,Muraoka, Osamu
, p. 1882 - 1890 (2010)
The methanolic extract from fresh stems of Cistanche tubulosa (Orobanchaceae) was found to show hepatoprotective effects against d-galactosamine (d-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. From the extract, three new phenylethanoid oligoglycosides, kankanosides H1 (1), H2 (2), and I (3), were isolated together with 16 phenylethanoid glycosides (4-19) and two acylated oligosugars (20, 21). The structures of 1-3 were determined on the basis of spectroscopic properties as well as of chemical evidence. Among the isolates, echinacoside (4, IC50 = 10.2 μM), acteoside (5, 4.6 μM), isoacteoside (6, 5.3 μM), 2′-acetylacteoside (8, 4.8 μM), and tubuloside A (10, 8.6 μM) inhibited d-GalN-induced death of hepatocytes. These five isolates, 4 (31.1 μM), 5 (17.8 μM), 6 (22.7 μM), 8 (25.7 μM), and 10 (23.2 μM), and cistantubuloside B1 (11, 21.4 μM) also reduced TNF-α-induced cytotoxicity in L929 cells. Moreover, principal constituents (4-6) exhibited in vivo hepatoprotective effects at doses of 25-100 mg/kg, po.
Three antibacterial compounds from the roots of Pteris multifida
Hao-Bin, Hu,Xu-Dong, Zheng,Huai-Sheng, Hu,Hong, Cao
, p. 45 - 48 (2009)
A new eudesmane-type sesquiterpenoid, 3β-caffeoxyl-1β,8α- dihydroxyeudesm-4(15)-ene (1), together with two known compounds including ludongnin V (2) and isoneorautenol (3), were isolated from the roots of Pteris multifida. Their structures were determined
A new naphthoquinone and a new neolignan from ligularia vellerea rhizomes
Wang,Zhao,Shi,Li,Zhang,Liu
, p. 184 - 186 (2010)
In the course of phytochemical investigations of Ligularia vellerea rhizomes, a new naphthoquinone, 2,5-dihydroxy-6,7-dimethylnaphthoquinone (1), and a new neolignan, 4-[(3',4'-dihydroxycinnamoyl)-oxy]-methyl cinnamate (2), have been isolated and characterized on the basis of spectroscopic methods (1H NMR, 13C NMR, 2D NMR, and MS).
Chemical structures of constituents from the whole plant of Bacopa monniera
Ohta, Tomoe,Nakamura, Seikou,Nakashima, Souichi,Oda, Yoshimi,Matsumoto, Takahiro,Fukaya, Masashi,Yano, Mamiko,Yoshikawa, Masayuki,Matsuda, Hisashi
, p. 404 - 411 (2016)
Two new dammarane-type triterpene oligoglycosides, bacomosaponins A and B, and three new phenylethanoid glycosides, bacomosides A, B1, and B2, were isolated from the whole plant of Bacopa monniera Wettst. The chemical structures of the new constituents were characterized on the basis of chemical and physicochemical evidence. In the present study, bacomosaponins A and B with acyl groups were obtained from the whole plant of B. monniera. This is the first report of acylated dammarane-type triterpene oligoglycosides isolated from B. monniera. In addition, dammarane-type triterpene saponins significantly inhibited the aggregation of 42-mer amyloid β-protein.
Phenylpropanoid glucosides from leaves of Coussarea hydrangeifolia (Rubiaceae)
Hamerski, Lidilhone,Bomm, Mauro Dionei,Silva, Dulce Helena Siqueira,Young, Maria Claudia Marx,Furlan, Maysa,Eberlin, Marcos Nogueira,Castro-Gamboa, Ian,Cavalheiro, Alberto Jose,Da Silva Bolzani, Vanderlan
, p. 1927 - 1932 (2005)
Phenylpropanoid glycosides, 1′-O-benzyl-α-l-rhamnopyranosyl- (1″ → 6′)-β-d-glucopyranoside (1) and α-l- xylopyranosyl-(4″ → 2′)-(3-O-β-d-glucopyranosyl)-1′- O-E-caffeoyl-β-d-glucopyranoside (2), together with the known derivatives, 1,6-di-O-caffeoyl-β-d-glucopyranoside (3), 1-O-(E)-caffeoyl-β-d- glucopyranoside (4) and 1-O-(E)-feruloyl-β-d-glucopyranoside (5), were isolated from leaves of Coussarea hydrangeifolia. Their structures were determined by IR, HRESIMS, and 1D and 2D NMR experiments, and their antioxidant activities, evaluated by assaying the free radical scavenging capacity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical as substrate. The antioxidant activities of 3 and 4 (IC50 values of 15.0 and 19.2 μM, respectively) were comparable to that of the standard positive control caffeic acid, whilst 2 and 5 were only weakly active and 1 was inactive.
Trisubstituted hydroxycinnamic acid spermidines from Quercus dentata pollen
Bokern,Witte,Wray,Nimtz,Meurer-Grimes
, p. 1371 - 1375 (1995)
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Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites
Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar
supporting information, p. 1929 - 1940 (2022/02/01)
The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had
Herbicide based on haloxyfop, flumetsulam and halosulfuron-methyl
-
Paragraph 0038; 0046; 0053; 0061; 0068; 0076, (2021/06/21)
The invention discloses a herbicide based on haloxyfop, flumetsulam and halosulfuron-methyl. The herbicide is prepared from the following raw materials in parts by weight: 1-15 parts of haloxyfop-R-methyl, 1-15 parts of flumetsulam, 1-37 parts of halosulfuron-methyl, 1-2 parts of a modified antioxidant, 10-12 parts of borax, 6-8 parts of a surfactant, 10-12 parts of triethanolamine, 10-12 parts of vegetable oil and 40-42 parts of deionized water. After the haloxyfop-R-methyl, the flumetsulam and the halosulfuron-methyl are mixed, the effects are complementary, the weeding spectrum is wider, the weeding activity is high, the weeding effect is more excellent. In addition, the modified antioxidant is added into the herbicide formula, so that the composite herbicide has the effects of resisting oxidation aging and ultraviolet aging, effective components are prevented from decomposing and losing efficacy in the presence of light, the pesticide effect is kept lasting, and the application prospect and popularization value are remarkably improved.