Cinnamic Acid
T-신남산 · 계피산 · 신나믹애씨드 · 3-PHENYLACRYLIC ACID · CINNAMIC ACID, TRANS- · 3-PHENYL-2-PROPENOIC ACID · FEMA 2288 · (2E)-3-phenylprop-2-enoic acid
식별자 및 물리적 특성
| CAS No. | 140-10-3 |
|---|---|
| 분자식 | C9H8O2 |
| 평균 분자량 | 148.16 g/mol |
| 단동위원소 질량 | 148.0524295 g/mol |
| SMILES | O=C(O)/C=C/c1ccccc1 |
| InChIKey | WBYWAXJHAXSJNI-VOTSOKGWSA-N |
| PubChem CID | 444539 |
| ChEMBL | CHEMBL27246 |
| ChEBI | CHEBI:27386 |
| EC No. | 205-398-1 |
| DTXSID | DTXSID5022489 |
| 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 |
| 물질 분류 | Other Classes -> Organic Acids |
| SpringerMaterials Properties | Angular frequency |
| 향료 | Fragrance Ingredient (Cinnamic acid) -> IFRA transparency ListFragrance Ingredient (trans-Cinnamic acid) -> IFRA transparency List |
| LogP(분배 계수) | 2.13 |
| 식품 첨가물 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 향미제 | EU Flavoring substances |
| 용해도 | 0.546 mg/mLinsoluble in watersoluble in oilsslightly soluble (in ethanol)0.4g/L |
| 끓는 점 | 298.00 to 300.00 °C. @ 760.00 mm Hg300 °C300 °C(lit.) |
| 녹는점 | 133 °C133 °C (lit.) |
| Physical Description | Solid with a honey floral odor[Merck Index] White crystalline solid[Alfa Aesar MSDS]White crystalline powder with a mild odorWhite crystalline scales, honey floral odour |
| Ionization Efficiency | Positive1.182.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Dissociation Constants | 4.45 |
| 밀도 | 1.248 |
| 증기압 | 1.3 hPa (128 °C) |
| 굴절률 | 1.5049 (estimate) |
| 인화점 | >230 °F |
| 저장 조건 | 2-8°C |
| pKa(산도 계수) | 4.44(at 25℃) |
| 물리적 상태 | 결정성 분말 |
| 색상 | 흰색에서 거의 흰색 |
| 비중 | 0.91 |
| 냄새 | 희미한 냄새 |
| pH | 3-4 (0.4g/l, H2O, 20℃) |
| 향취 유형 | 발사믹 |
| 생물학적 소스 | synthetic |
| 용해도 | 0.4g/L(20℃) |
| Merck | 14,2299 |
| BRN | 1905952 |
| 헨리 상수 | 2.8×1011 mol/(m3Pa) at 25℃, Abraham and Jr. (2019) |
| 안정성 | 감광성 |
| 주요 응용 | 향료 및 향 |
| 화장품 원료 기능 | 향수피부 컨디셔닝 |
| InChI | 1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ |
| InChIKey | WBYWAXJHAXSJNI-VOTSOKGWSA-N |
| SMILES | OC(=O)\C=C\c1ccccc1 |
| LogP(분배 계수) | 2.130 |
| NIST | Cinnamic acid(140-10-3) |
| EPA | (E)-Cinnamic acid (140-10-3) |
화학적 성질
White to almost white crystalline powder. Insoluble in water, slightly soluble in hot water, easily soluble in benzene, acetone, ether, glacial acetic acid and other organic solvents.
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 97.8% (1644 of 1681) of all reports.Not ClassifiedAggregated GHS information provided per 1681 reports by companies from 7 notifications to the ECHA C&L Inventory.This chemical does not meet GHS hazard criteria for 76.1% (284 of 373) of all reports.WarningH315 (15.5%): Causes skin irritation [Warning Skin corrosion/irritation] |
|---|---|
| 규제 정보 | Chemical: 2-Propenoic acid, 3-phenyl-, (E)-Chemical: 2-Propenoic acid, 3-phenyl-Regulation (EC) No 1831/2003 (amended)Status: Active Update: 06-02-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/238162-Propenoic acid, 3-phenyl-, (E)-: Does not have an individual approval but may be used under an appropriate group standardCinnamic 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 |
| 유해성 요약 | A mild skin irritantCauses gastrointestinal changes in acute oral studies of rats[RTECS] Safe when used as a flavoring agent in food[JECFA] An eye irritant[Alfa Aesar MSDS] See Hydrocinnamic acid.A mild skin and strong eye irritant |
| Hazard Classes and Categories | Skin Irrit. 2 (15.5%)Not Classified |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 수질 위해 등급(WGK) | 1 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | GD7850000 |
| 독성 | LD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| 관세 코드 | 29163900 |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26-36-37/39 |
| 기존화학 물질 | KE-28423 |
| 위험 등급 | Eye Irrit. 2 |
| 저장 분류 | 13 - Non Combustible Solids |
용도
용도
trans-Cinnamic acid is used in flavors, synthetic indigo and pharmaceuticals. It is involved in the production of methyl, ethyl and benzyl esters, which is used in the perfume industry. It serves as a precursor to the sweetener aspartame through enzyme-catalyzed amination to phenylalanine. It is a self-inhibitor produced by fungal spores to prevent germination. In addition, it is used to establish phenolic compounds by liquid chromatography, ultraviolet and mass spectrometry. It is utilized as a potential agent, thereby preventing lung tumor cells from metastasizing. Further, it induces intracellular release of calcium ions from the vacuole to the cytoplasm in order to trigger phytotoxicity in cucumber.
일반 설명
trans-Cinnamic acid is an α,β-unsaturated aromatic acid that can be used as a flavoring agent. It is mainly used to prepare ester derivatives that are used in perfume industry. trans-Cinnamic acid is the key volatile components of cinnamon essential oil.