3-(3,4-dihydroxyphenyl)prop-2-enoic acid
3,4-Dihydroxycinnamic acid
CAS: 331-39-5
Molecular Formula: C9H8O4
3-(3,4-dihydroxyphenyl)prop-2-enoic acid - Names and Identifiers
| Name | 3,4-Dihydroxycinnamic acid |
| Synonyms | Caffeicacid Caffeic acid CAFFEIC ACID TIMTEC-BB SBB006475 RARECHEM BK HC T335 3,4-Dihydroxycinnamic acid 3-(3,4-DIHYDROXYPHENYL)ACRYLIC ACID 3-(3,4-dihydroxyphenyl)prop-2-enoic acid 4-(2'-carboxyvinyl)-1,2-dihydroxybenzene 3-(3,4-DIHYDROXYPHENYL)-2-PROPENOIC ACID 4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid |
| CAS | 331-39-5 |
| EINECS | 206-361-2 |
| 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+ |
| InChIKey | QAIPRVGONGVQAS-DUXPYHPUSA-N |
3-(3,4-dihydroxyphenyl)prop-2-enoic acid - Physico-chemical Properties
| Molecular Formula | C9H8O4 |
| Molar Mass | 180.16 |
| Density | 1.2933 (rough estimate) |
| Melting Point | 211-213 °C (dec.) (lit.) |
| Boling Point | 272.96°C (rough estimate) |
| Flash Point | 220°C |
| Water Solubility | soluble in hot water |
| Solubility | Slightly soluble in cold water, easily soluble in hot water and cold ethanol |
| Vapor Presure | 1.08E-07mmHg at 25°C |
| Appearance | Yellow crystal |
| Color | yellow to tan |
| Merck | 14,1635 |
| BRN | 2210883 |
| pKa | 4.58±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.4500 (estimate) |
| MDL | MFCD00004392 |
| Physical and Chemical Properties | Yellow crystal. melting point 195 ℃ solubility: soluble in hot water and ethanol. |
| Use | Used as a reagent for organic synthesis |
3-(3,4-dihydroxyphenyl)prop-2-enoic acid - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R40 - Limited evidence of a carcinogenic effect R63 - Possible risk of harm to the unborn child R68 - Possible risk of irreversible effects |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | GD8950000 |
| HS Code | 29182990 |
| Hazard Note | Irritant |
3-(3,4-dihydroxyphenyl)prop-2-enoic acid - Reference Information
| update date: | 2022/11/12 12:49:22 |
| (IARC) carcinogen classification | 2B (Vol. 56) 1993 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | caffeic acid is widely distributed in many kinds of traditional Chinese medicine plants such as artemisia, thistle, honeysuckle, etc. It belongs to phenolic acid compounds and has pharmacological effects such as cardiovascular protection, anti-mutagenesis and anti-cancer, antibacterial and antiviral, lipid-lowering and glucose-lowering, anti-leukemia, immune regulation, choleretic hemostasis and anti-oxidation. |
| Application | Caffeic acid is widely distributed in many traditional Chinese medicine plants such as Artemisia artemisiae, vegetable thistle, honeysuckle, etc. It belongs to phenolic acid compounds and has cardiovascular protection, anti-mutagenic and anti-cancer, antibacterial and antiviral, lipid-lowering, hypoglycemic, anti-leukemia, immune regulation, choleretic hemostasis and antioxidant. Caffeic acid can contract and strengthen microvessels, reduce permeability, improve coagulation function and the number of white blood cells and platelets. It is often used in the prevention and treatment of various surgical and medical bleeding clinically. It has a significant effect on gynecological bleeding diseases and is also used for tumor diseases. Leukocyte thrombocytopenia symptoms caused by chemotherapy and radiotherapy and other reasons also have certain effects on primary thrombocytopenia and aplastic leukopenia. |
| extraction method | caffeic acid is a common phenolic acid compound, which has the effect of promoting white blood cells and is easily confused with caffeine. It is common in the plant kingdom, mainly from lemon peel, Ranunculaceae plant cimicifuga rhizome, valerian root and other plants. Caffeic acid, ferulic acid, sinapic acid, and p-hydroxycinnamic acid are almost ubiquitous in plants. There are conjugated double bonds on the side chain of the molecular structure of such products, which are fluorescent under ultraviolet light. Most of them are blue fluorescent. This is a favorable condition for paper chromatography or thin layer chromatography examination. Extraction method: The rhizome of hemp with single spike was extracted with methanol, and the methanol was concentrated under reduced pressure. The residue is heated with water to dissolve, and the insoluble matter is filtered out while it is hot. After cooling, benzene is added for extraction, and the benzene solution is washed with 1% sodium bicarbonate aqueous solution to collect the washing liquid. Add dilute hydrochloric acid to acidify, use benzene and then free organic acid from it, concentrate to remove benzene under reduced pressure, and the residue is caffeic acid enriched product. |
| leukocyte-raising drug | caffeic acid is also a hemostatic leukocyte-raising drug, which has the functions of contracting and coagulating capillaries, improving coagulation factor function, and increasing leukocytes and platelets. It is suitable for preventing bleeding or hemostasis during surgery, as well as bleeding diseases such as internal medicine, obstetrics and gynecology. It is also used for leukopenia and thrombocytopenia caused by various reasons. |
| HPLC determination of caffeic acid content in dandelion | [test article] chrysanthemum plant dandelion Taraxacum mongolicum Hand. Mazz., dandelion t. sinicum Kitag. (1) chromatographic conditions: decyl silane bond containing silica gel is used as filler; Methanol-phosphate buffer solution (1.56g sodium dihydrogen phosphate, add water to dissolve into 1000ml, add 1% phosphoric acid solution to adjust the pH value to 3.8~4.0 to obtain) (23:77) is the mobile phase; The detection wavelength is 323nm; The column temperature is 40 ℃. The number of theoretical plates is calculated by caffeic acid peak and is not less than 3000. (2) preparation of reference substance solution: take 7.5mg of caffeic acid reference substance, weigh it accurately, place it in a 50ml volumetric flask, add methanol to scale, shake well; Accurately measure 2ml, place it in a 10ml volumetric flask, add methanol to scale, shake well, and obtain (caffeic acid 30 μg per ml). (3) preparation of sample solution: take about 1g of medicinal powder, weigh it accurately, place it in a 50ml conical flask with plug, add 10ml of 5% formic acid methanol solution accurately, plug it tightly, shake well, weigh it well, treat it with ultrasound for 30min, take it out, cool it, weigh it again, supplement the lost weight with 5% formic acid methanol solution, shake well, centrifuge, and take the supernatant, filtered with a microporous filter membrane (0.45 μm), and the filtrate is placed in a brown bottle to obtain. (4) determination method: 10 μl of reference substance solution and 10 μl of sample solution are accurately absorbed respectively, injected into liquid chromatograph for determination. (5) determination results: dandelion medicinal materials contain not less than 0.02% caffeic acid according to dry products. |
| preparation | preparation of caffeic acid crude product 30 g3, 4-dihydroxybenzaldehyde, 60.0g malonic acid is added with 300mlN,N-dimethylformamide to dissolve, 45mL pyridine is added, and then the temperature is increased to 70 ℃. Add 9mL aniline and react for 1 hour. After the reaction is over, the reaction solution is cooled to below 30 ℃, 1000 ml2moL/L hydrochloric acid is added for stirring, and crystallization is stirred at room temperature for 2 hours. Suction filtration, filter cake with 300ml purified water wash twice. 36.50g of crude yellow caffeic acid was obtained by blowing and drying at 50 ℃, with a yield of 93.60%, 99.52% purity and 99.2% content. Caffeic acid refining 30g of crude caffeic acid and 120ml of ethanol are added into a 500mL four-mouth bottle, heated to 80 ℃, stirred until dissolved, 1.5g of activated carbon is added to decolorize for 15min, and then filtered while hot. The filtrate was cooled to 5-10 ℃ and stirred for 2h. Suction filtration, filter cake with 60ml purified water wash. 27.39g of light yellow caffeic acid refined product was obtained by drying at 50 ℃ with a yield of 91.30%, 99.83% purity and 99.8% content. |
| Use | As an intermediate, it can be used in organic synthesis. a natural phenolic acid compound found in plants is an antioxidant that inhibits the synthesis of leukotrienes (leukotrienes) (leukotrienes are involved in the regulation of immunity, inflammation and sensitivity), and inhibits Cu2-induced oxidation of LDL. Antioxidant natural dietary phenolic compounds found in plants. Suppresses the synthesis of leukotrienes involved in immune regulation, inflammation and allergy. Cu2 +-induced LDL oxidation was also inhibited. |
| production method | 1. the rhizome of hemp with a single spike is extracted with methanol and concentrated to remove methanol under reduced pressure. The residue is dissolved in heated water and the insoluble matter is filtered out while it is hot. After cooling, benzene is added for extraction, and the benzene solution is washed with 1% sodium bicarbonate aqueous solution to collect the washing liquid. Add dilute hydrochloric acid to acidify, use benzene to free organic acid from it, concentrate to remove benzene under reduced pressure, and the residue is caffeic acid enriched product. 2. Tobacco: FC,53, 54. It is obtained by acid hydrolysis of chlorogenic acid. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | abdominal cavity-rat LDL0: 1500 mg/kg |
| flammability hazard characteristics | thermal decomposition spicy stimulation smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | water, dry powder, carbon dioxide, foam |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:41:03
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