140-10-3
trans-Cinnamic acid
CAS: 140-10-3;621-82-9
Molecular Formula: C9H8O2
140-10-3 - Names and Identifiers
| Name | trans-Cinnamic acid |
| Synonyms | Cinnamic acid trans-Ciamic acid Phenylacrylic acid (e)-2-propenoicaci trans-Cinnamic acid β-phenylacrylic acid 3-Phenylacrylic acid Nat.trans-Cinnamic acid CINNAMIC ACID, TRANS-(SG) 3-phenylprop-2-enoic acid trans-3-Phenylacrylic acid (2E)-3-phenylprop-2-enoate trans-Cinnamicacid 140-10-3 (E)-3-Phenyl-2-propenoic acid (2Z)-3-phenylprop-2-enoic acid (2E)-3-phenylprop-2-enoic acid trans-3-Phenyl-2-propenoic acid 2-{[(3alpha,5beta,6beta,7beta,8xi,9xi,14xi)-3,6,7-trihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid |
| CAS | 140-10-3 621-82-9 |
| EINECS | 205-398-1 |
| InChI | InChI=1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6- |
| InChIKey | WBYWAXJHAXSJNI-VOTSOKGWSA-N |
140-10-3 - Physico-chemical Properties
| Molecular Formula | C9H8O2 |
| Molar Mass | 148.16 |
| Density | 1.248 |
| Melting Point | 133 °C (lit.) |
| Boling Point | 300°C(lit.) |
| Flash Point | >230°F |
| Water Solubility | 0.4 g/L (20 ºC) |
| Solubility | Soluble in ethanol, methanol, petroleum ether, chloroform, easily soluble in benzene, ether, acetone, glacial acetic acid, carbon disulfide and oils, slightly soluble in water. |
| Vapor Presure | 1.3 hPa (128 °C) |
| Appearance | White powder |
| Specific Gravity | 0.91 |
| Color | White to almost white |
| Odor | Faint odour |
| Maximum wavelength(λmax) | ['273nm(MeOH)(lit.)'] |
| Merck | 14,2299 |
| BRN | 1905952 |
| pKa | 4.44(at 25℃) |
| PH | 3-4 (0.4g/l, H2O, 20℃) |
| Storage Condition | 2-8°C |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.5049 (estimate) |
| MDL | MFCD00004369 |
| Physical and Chemical Properties | Trait: white monoclinic prism. There is a micro cinnamon aroma. density 1.248 melting point 135~136 ℃ boiling point 300 ℃ relative density 1.2475 soluble in ethanol, methanol, petroleum ether, chloroform, soluble in benzene, ether, acetone, acetic acid, carbon disulfide and oil, insoluble in water. |
| Use | Is the preparation of esters, spices, medicine raw materials |
140-10-3 - 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 | 1 |
| RTECS | GD7850000 |
| TSCA | Yes |
| HS Code | 29163900 |
| Toxicity | LD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
140-10-3 - Upstream Downstream Industry
| Downstream Products | L-Phenylalanine |
140-10-3 - Nature
Open Data Verified Data
take the trans isomer as an example. White monoclinic prisms. There is a micro cinnamon aroma. Soluble in ethanol, methanol, petroleum ether, chloroform, soluble in benzene, ether, acetone, acetic acid, carbon disulfide and oil, insoluble in water. Flammable. Can be volatile with steam. The relative density was 1. 2475. The melting point was 135-136 °c. Boiling point 300 °c.
Last Update：2025-06-10 22:55:16
140-10-3 - Preparation Method
Open Data Verified Data
benzaldehyde and acetic anhydride are heated in the presence of sodium acetate (155 ℃). After the reaction is completed, the benzaldehyde is distilled out by steam, then neutralized by caustic soda, and centrifuged to obtain sodium cinnamate and sodium acetate solution, by acid analysis of cinnamic acid, boiling water recrystallization, that is, the refined products.
Last Update：2022-01-01 10:43:34
140-10-3 - Application
Open Data Verified Data
It is mainly used for the preparation of esters, for the preparation of clove-type flower fragrance and as an intermediate for medicine (xincrestor). It can also be used as a reagent for the determination of uranium and vanadium.
Last Update：2025-08-19 16:24:40
140-10-3 - Safety
Open Data Verified Data
- This product has low toxicity. Rat oral LD502500mg/kg, mouse oral LD50160mg/kg.
- the use of lined plastic film bag, external polypropylene woven bag packaging, each bag lokg.
Last Update：2022-01-01 10:43:35
140-10-3 - Reference Information
| Plant source: | Cinnamon |
| pH indicator color change ph range | 3-4 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | cinnamic acid is also called cinnamic acid and cinnamic acid. Molecular structure: C6H5CHCHCOOH, English Trans2Cinnamicacid, white monoclinic crystal in appearance, slightly cinnamon smell. Cinnamic acid is an important intermediate in fine chemical synthesis, which is widely used in chemical products such as medicine, perfume, plastic and photosensitive resin. There are two isomers, cis and trans, usually in trans. Slightly soluble in water, easily soluble in acid, benzene, acetone, glacial acetic acid, soluble in ethanol, methanol and chloroform. When cinnamic acid is heated, styrene is decarboxylated, and benzoic acid is formed when oxidized. Cinnamic acid exists in Toru balsam, Suhe balsam, etc. Cinnamic acid is mainly used to make esters, for the preparation of lilac type and other floral essence and medicine. |
| uses and functions of cinnamic acid (in essence and spice) | 1. prepare apples, cherries, and can be used as apple essence, cherry essence, fruit essence and flower essence. 2. It can be used as an aromatic mixture in soap, shampoo, washing powder and daily cosmetics. 3. It has the effect of inhibiting the formation of black tyrosinase, has a certain isolation effect on ultraviolet rays, and can make brown spots lighter or even disappear. It is one of the indispensable ingredients in advanced sunscreen. 4. Cinnamic acid itself is a kind of spice, which has a good fragrance preservation effect. It is usually used as a raw material to make the aroma of the main spice more fragrant and volatile. Various esters of cinnamic acid (such as A, B, C, D, etc.) can be used as a fixer for beverages, cold drinks, candy, alcohol and other foods. |
| in food additives | 1. cinnamic acid uses microbial enzymatic synthesis of L-phenylalanine. L-phenylalanine is the main raw material of sweet aspartame (Aspartame), an important food additive. 2. Unilever of the United Kingdom has obtained the World Intellectual Property Organization patent PCTInt. Appl. Wo01 87,080(2001,11.22) This article introduces the composition of cinnamic acid and pasteurization additives, which have strong sterilization and antiseptic effects. 3. Cinnamic acid is also a component of capsaicin synthase-cinnamic acid hydrolase, which can be used to cultivate excellent varieties of capsaicin with high-yield capsaicin content, which will greatly improve the quality of capsicum and effectively promote the industrialization of capsicum. 4. The use of cinnamic acid to prevent mildew, preservative and sterilization can be applied to the preservation and preservation of grains, vegetables and fruits. 5. It can also be used in wine to make it bright in color. 6. Cinnamic acid has a strong excitatory effect and can be widely and directly added to all foods. |
| in the pharmaceutical industry | in the pharmaceutical industry, lactic acid, an important drug for the treatment of coronary heart disease, can be synthesized. It can also synthesize chlorphenambutyric acid and cinnamon phenoperazine, which are used as spinal cone bone relaxants and antispasmodics. Mainly used for cerebral thrombosis, cerebral arteriosclerosis, coronary arteriosclerosis and other diseases. It has obvious inhibitory effect on the proliferation of lung adenocarcinoma cells. Cinnamic acid is an effective inhibitor for the A- 5491 of human lung adenocarcinoma cells and has great application value in anti-cancer. |
| in beauty | cinnamic acid can be used in beauty. casinase is the key enzyme for melanin synthesis. it initiates the level chain reaction from tyrosine to melanin biopolymer. cinnamic acid has the effect of inhibiting the formation of black tyrosinase, has a certain isolation effect on ultraviolet rays, and can make brown spots lighter or even disappear, it is one of the essential ingredients in advanced sunscreen. The significant antioxidant effect of cinnamic acid has a good effect on slowing down the appearance of wrinkles. |
| In the pesticide industry | In the agricultural industry, cinnamic acid is used as a growth promoter and long-acting fungicide for fruit and vegetable preservation. |
| in organic synthesis and chemical engineering | in organic chemical synthesis, cinnamic acid can be used as a slow-release agent for galvanized sheet, a heat stabilizer for polyvinyl chloride, a crosslinking agent for polycarbamate, a flame retardant for hydanyl and polycaprolactam, and a chemical analysis reagent. It is also a reagent for determining the separation of uranium and vanadium; it is also the most important synthetic raw material for negative photosensitive resins. The main synthesis of cinnamic acid ester, polyvinyl cinnamic acid ester, polyethylene oxycinnamic acid ethyl ester and the side group for the epoxy resin of cinnamic acid ester. Used in plastics, it can be used as a heat stabilizer for PVC, sterilization, anti-mold and deodorant, and can also be added in rubber and foam plastics to make anti-odor shoes and insoles, and can also be used in cotton cloth and various synthetic fibers, leather, Paint, shoe polish, straw mat and other products to prevent mildew. |
| Uses | Cinnamic acid, also known as phenylacrylic acid, is an intermediate of rodenticide bromadiolone. Cinnamic acid is used to prepare L-phenylalanine, as an intermediate for coronary heart disease medicine Xinkean, and can also be used to make local anesthetics, fungicides, hemostatic drugs, etc.; it is used in the perfume industry to prepare phenyl methyl acrylate, ethyl ester and phenyl ester, used as food and cosmetic spices, and has a better fragrance-preserving effect; used for pesticide industry growth promoters, long-acting fungicides, preservatives for fruits and vegetables, etc.; also used in the production of photosensitive resins The main raw material vinyl cinnamic acid. Cinnamic acid is a reagent for the determination of uranium, vanadium and the separation of thorium. It is often used as a cream or a fixative, especially suitable for oriental fragrance. Among the edible flavors, it is mostly used for spices such as cinnamon, and occasionally used in cherries and honey flavors. Cinnamic acid can be used to synthesize chloramphenicol cinnamate, cardiostat, etc., and can also be used to prepare anesthetics, fungicides and hemostatic drugs. In the perfume industry, it can be widely used to synthesize methyl cinnamate, ethyl cinnamate and phenyl cinnamate. Determination of uranium and vanadium, separation of thorium, and production of cinnamic acid esters. Standard for the determination of double bonds by organic microanalysis. |
| production method | is obtained by condensation of benzaldehyde and acetic anhydride. Benzaldehyde, acetic anhydride and sodium acetate are put into a dry glass-lined reaction pot, stirred and heated, and refluxed for 7-9h. Acetic acid is recovered at normal pressure to 140 ℃, and acetic anhydride is recovered at reduced pressure until the material is viscous. Dissolve with heated water, and recover unreacted benzaldehyde by steam distillation until no oil is evaporated. Add water and liquid alkali to dissolve, add activated carbon, and reflux at 100 ℃ for 15min. Filter while hot. The filtrate is neutralized with hydrochloric acid to pH = 1, cooled to 10 ℃, crystallized, filtered and dried to obtain cinnamic acid. 58% yield. the preparation method is to add benzaldehyde, acetic anhydride and anhydrous sodium acetate in the reactor, heat at 180 ℃ for 8 h, then cool to 80~100 ℃, pour into water, carry out steam distillation, remove unreacted benzaldehyde, add appropriate amount of hydrochloric acid to acidify the solution after distillation, and precipitate the product. |
Last Update：2024-04-09 20:52:54
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