계피산
신남산 · cinnamic · Phenylacrylic acid · 3-PHENYLPROPENOIC ACID · 3-PHENYLACRYLIC ACID · CINNAMIC ACID, TRANS- · Zimtsaeure · FEMA 2288
식별자 및 물리적 특성
| CAS No. | 621-82-9 |
|---|---|
| 분자식 | C9H8O2 |
| 평균 분자량 | 148.16 g/mol |
| 단동위원소 질량 | 148.0524295 g/mol |
| SMILES | O=C(O)C=Cc1ccccc1 |
| InChIKey | WBYWAXJHAXSJNI-UHFFFAOYSA-N |
| PubChem CID | 8784 |
| DTXSID | DTXSID40110056 |
| 현지명 | 계피산 |
화학 및 물리적 성질
| XLogP | 2.1 |
|---|---|
| 극성 표면적 | 37.3 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 155 |
| LogP(분배 계수) | 2.37 |
| 용해도 | insoluble in watersoluble in oilsslightly soluble (in ethanol)클로로포름(약간 용해됨), 메탄올(약간 용해됨) |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 끓는 점 | 300 °C300 °C(lit.) |
| Physical Description | White crystalline scales, honey floral odour |
| 녹는점 | 133 °C(lit.) |
| 밀도 | 1.2475 |
| 굴절률 | 1.5049 (estimate) |
| FEMA | 2288 | CINNAMIC ACID |
| 인화점 | >230 °F |
| 저장 조건 | Sealed in dry,Room Temperature |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | pK (25°) 4.46 |
| 색상 | 흰색에서 황백색까지 |
| pH | 3.76(1 mM solution)3.23(10 mM solution)2.72(100 mM solution) |
| 냄새 | 100.00%에서. 발삼 달콤한 스토락스 |
| 향취 유형 | 발사믹 |
| 용해도 | 511.2mg/L(25 ºC) |
| JECFA Number | 657 |
| 헨리 상수 | 5.8×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 안정성 | 안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다. |
| 화장품 원료 기능 | 피부 컨디셔닝향수 |
| LogP(분배 계수) | 2.13 |
| NIST | 2-Propenoic acid, 3-phenyl-(621-82-9) |
| EPA | Cinnamic acid (621-82-9) |
화학적 성질
Cinnamic acid is almost odorless with a burning taste, and then turning sweet and reminiscent of apricot.
안전 및 규제
| 규제 정보 | Chemical: 2-Propenoic acid, 3-phenyl-Cinnamic acid: Does not have an individual approval but may be used under an appropriate group standard |
|---|---|
| 기타 안전 정보 | IMAP assessments - Cinnamic acid: Human health tier II assessment |
| 수질 위해 등급(WGK) | 1 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | GD7850000 |
| 독성 | LD50 (g/kg): 3.57 orally in rats>5.0 dermally in rabbits (Letizia) |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26-36 |
| 기존화학 물질 | KE-28426 |
용도
개요
Cinnamic acid is a white crystalline organic acid, which is slightly soluble in water. It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter and is the best indication of its environmental history and post-extraction conditions. It can also be made synthetically. Cinnamic acid is used in flavors, synthetic indigo, and certain pharmaceuticals, though its primary use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry. Cinnamic acid has a honey- like odor; it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent. Cinnamic acid is also part of the biosynthetic shikimate and phenyl propanoid pathways. Its biosynthesis is performed by action of the enzyme phenylalanine ammonia - lyase (PAL) on phenylalanine. Cinnamic acid is freely soluble in benzene, diethyl ether, acetone, and it is insoluble in hexane. Cinnamic acid is also a kind of self-inhibitor produced by fungal spore to prevent germination.
출처
The trans- form has been found among the constituents of the essential oils of basil, Chinese cinnamon, Melaleuca bracteata, Alpinia galanga. It is reported found in Peru balsam, Asian and American storax and cocoa leaves. Also reported found in strawberry fruit, beer, cognac, starfruit (Averrhoa carambola L) and loquat. The cis- form is present in the oil of Alpinia malacensis.
용도
cinnamic acid has sunscreen capabilities. Some manufacturers use it to replace PABA because of its lower allergic and phototoxic reaction incidence. Cinnamic acid is found in cinnamon leaves and cocoa leaves, and is an essential oil of certain mushrooms. It may cause allergic skin rashes.
제조 및 합성 방법
제조 방법
Two isomers, trans- and cis- exist; the trans-isomer is of interest for use in flavoring; in addition to the extraction from natural sources (storax), it can be prepared as follows: (1) from benzaldehyde, anhydrous sodium acetate and acetic anhydride in the presence of pyridine (Perkin reaction); (2) from benzaldehyde and ethyl acetate (Claisen condensation); (3) from benzaldehyde and acetylene chloride; (4) by oxidation of benzylidene acetone with sodium hypochlorite.