3-(4-Hydroxy-3-methoxyphenyl)acrylic acid
4-Hydroxy-3-methoxycinnamic acid
CAS: 1135-24-6
Molecular Formula: C10H10O4
3-(4-Hydroxy-3-methoxyphenyl)acrylic acid - Names and Identifiers
| Name | 4-Hydroxy-3-methoxycinnamic acid |
| Synonyms | Ferulic acid AKOS BBS-00006472 RARECHEM BK HW 0087 TIMTEC-BB SBB000326 OTAVA-BB BB7016261120 3-METHOXY-4-HYDROXYCINNAMIC ACID 4-Hydroxy-3-methoxycinnamic acid 4-HYDROXY-3-METHOXYCINNAMIC ACID 3-(4-HYDROXY-3-METHOXYPHENYL)ACRYLIC ACID 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid 3-(4-hydroxy-3-methoxyphenyl)-2-Propenoic acid4-Hydroxy-3-methoxycinnamic acid |
| CAS | 1135-24-6 |
| EINECS | 214-490-0 |
| InChI | InChI=1/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/p-1/b5-3+ |
| InChIKey | KSEBMYQBYZTDHS-HWKANZROSA-N |
3-(4-Hydroxy-3-methoxyphenyl)acrylic acid - Physico-chemical Properties
| Molecular Formula | C10H10O4 |
| Molar Mass | 194.18 |
| Density | 1.316(20.0000℃) |
| Melting Point | 168-172°C(lit.) |
| Boling Point | 250.62°C (rough estimate) |
| Flash Point | 150.5°C |
| Water Solubility | soluble |
| Solubility | Soluble in hot water, ethanol and ethyl acetate, easily soluble in ether, slightly soluble in petroleum ether and benzene. |
| Vapor Presure | 0Pa at 25℃ |
| Appearance | The cis isomer is yellow oil. The trans isomer is an oblique grain crystal (water). |
| Color | slightly yellow |
| pKa | 4.58±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.5168 (estimate) |
| MDL | MFCD00004400 |
| Physical and Chemical Properties | The trait cis-isomer was yellow oil. The trans isomer is an oblique Crystal (water). melting point 174 ℃ solubility: soluble in hot water, ethanol and ethyl acetate. More soluble in ether, benzene-soluble and petroleum ether. |
| Use | Used as food preservatives and raw materials for organic synthesis |
3-(4-Hydroxy-3-methoxyphenyl)acrylic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | UD3365500 |
| HS Code | 29162090 |
| Hazard Class | IRRITANT |
3-(4-Hydroxy-3-methoxyphenyl)acrylic acid - Reference
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3-(4-Hydroxy-3-methoxyphenyl)acrylic acid - Reference Information
| LogP | 1.51 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Uses | Ferulic acid has many health functions, such as scavenging free radicals, anti-thrombosis, antibacterial and anti-inflammatory, inhibiting tumors, preventing and treating hypertension, heart disease, and enhancing sperm motility, etc.; And its toxicity is low, it is easy to metabolize for the human body, can be used as a food preservative, and has a wide range of uses in food, medicine, etc. Used as a food preservative and organic synthesis raw material An intermediate of cholinic acid. Food preservatives. |
| Plant source | Ferulic acid is a phenolic acid extracted from the resin of Ferulia. Ferulic acid is a perennial herb of the Umbelliferae family. It stinks of garlic and is born in sandy areas. It is mainly produced in Xinjiang. It only has root leaves when it first grows, and it starts to pump flower stems in the fifth year. The flower stem is thick, up to 2 meters high; from the full flowering period to the first fruit period in late spring and early summer, it is cut obliquely from the upper part of the stem to the bottom, and the exuded milky resin is collected and dried in the shade. Ferula contains volatile oil, resin and gum, etc. The oil contains a variety of organic acids, such as (R)-sec-butyl 1-propenyl disulfide, 1 (1-methylthiopropyl) 1-propenyl disulfide, sec-butyl 3-methylthioallyl disulfide, etc. The resin contains ferulic acid and its esters. Fig. 1 is ferula |
| lowering blood lipid | ferulic acid can competitively inhibit the activity of hydroxyvalonate -5-pyrophosphate dehydrogenase in liver and inhibit the synthesis of cholesterol in liver, thus achieving the purpose of lowering blood lipid. |
| bacteriostasis | ferulic acid has a broader inhibitory effect on bacteria. it has been found that ferulic acid can inhibit the reproduction of pathogenic bacteria such as Shigella sonnei, pneumobacteria, enterobacter, Escherichia coli, citrate, Pseudomonas aeruginosa and 11 microorganisms that cause food spoilage. |
| food industry application | ferulic acid is widely used in medicine, some countries have approved it as a food additive. Japan has allowed food antioxidants, while the United States and some European countries have allowed the use of herbs, coffee, vanilla beans, etc. that contain higher amounts of ferulic acid as antioxidants. Ferulic acid is mainly used to prepare natural vanillin, antioxidant, preservative, crosslinking agent and function promoter in food industry. |
| pharmacological action | ferulic acid has the effects of inhibiting platelet aggregation, expectorant, inhibiting tuberculosis, etc. Clinically, ferulic acid is mainly used for adjuvant treatment of arteriosclerosis, coronary heart disease, cerebrovascular, glomerular disease, pulmonary hypertension, diabetic vascular disease, vasculitis and other vascular diseases, as well as leukopenia and thrombocytopenia. It can be used for the treatment of migraine and vascular headache. As a leukocyte-raising drug, this drug also has the effect of enhancing hematopoietic function. Therefore, ferulic acid can also be used for the treatment of leukocytes and thrombocytopenia. Reference materials: Xu Jingfeng, edited by Yang Benming. Manual of Clinical Prescription Drugs. Nanjing: Jiangsu Science and Technology Press. 2009. p. 561. |
| Synthesis method | Ferulic acid can be obtained by chemical synthesis and extraction. The laboratory dissolves vanillin, malonic acid and pinidine in pyridine, After 3 weeks of reaction, ferulic acid can be obtained by precipitation with hydrochloric acid. fig. 2 is a roadmap for laboratory synthesis of ferulic acid |
| preparation | (1) extracted from plant materials with high ferulic acid content such as angelica, vanilla bean, wheat bran and rice bran, and then obtained ferulic acid by alkaline hydrolysis or enzymatic hydrolysis. (2) Chemical synthesis: vanillin and malonic acid are used as raw materials to synthesize by Kno- evngael reaction. (3) Biosynthesis: Using some microorganisms, ferulic acid precursor substances are transformed to obtain ferulic acid. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:47
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