하이드록시시트로넬랄
7-하이드록시-3,7-디메틸옥탄 · 하이드록시시트로넬랄 · 하이드록시시트로넬알 · Lilyl aldehyde · Cyclosia · 7-HYDROXYCITRONELLAL · LAURINE · OCTANAL, 7-HYDROXY-3,7-DIMETHYL
식별자 및 물리적 특성
| CAS No. | 107-75-5 |
|---|---|
| 분자식 | C10H20O2 |
| 평균 분자량 | 172.26 g/mol |
| 단동위원소 질량 | 172.14632988 g/mol |
| SMILES | CC(CC=O)CCCC(C)(C)O |
| InChIKey | WPFVBOQKRVRMJB-UHFFFAOYSA-N |
| PubChem CID | 7888 |
| ChEMBL | CHEMBL3186027 |
| ChEBI | CHEBI:53459 |
| EC No. | 203-518-7 |
| DTXSID | DTXSID6042232 |
| 현지명 | 하이드록시시트로넬랄 |
화학 및 물리적 성질
| XLogP | 1.6 |
|---|---|
| 극성 표면적 | 37.3 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 6 |
| 무거운 원자 수 | 12 |
| 형식 전하 | 0 |
| 복잡도 | 130 |
| 물질 분류 | Biological Agents -> Plant Oils and Extracts |
| 화장품 | Cosmetics ingredient -> BaseFlavorFragranceMoisturizing/HumectantOther (Specify)Masking |
| 향료 | Fragrance Ingredient (Hydroxycitronellal) -> IFRA transparency List |
| 식품 첨가물 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 밀도 | 0.918-0.9230.923 g/mL at 25 °C(lit.) |
| 향미제 | EU Flavoring substances |
| 용해도 | slightlyslightly soluble in watersoluble in alcohol, propylene glycol, and oilsinsoluble in glycerol1 ml in 1 ml 50% alcohol (in ethanol)벤젠(약간 용해됨), 클로로포름(약간 용해됨), 메탄올(약간 용해됨) |
| 끓는 점 | 241.00 °C. @ 760.00 mm Hg241 °C94-96 °C (1 mm Hg)257 °C(lit.) |
| 굴절률 | 1.447-1.450n20/D 1.448(lit.) |
| Physical Description | LiquidDry PowderCBI[Sigma-Aldrich MSDS]colourless liquid with sweet floral lily-like odour |
| 녹는점 | 22-23 °C |
| 증기압 | 0.547Pa at 20℃ |
| FEMA | 2583 | HYDROXYCITRONELLAL |
| 인화점 | >230 °F |
| 저장 조건 | Inert atmosphere,Store in freezer, under -20°C |
| pKa(산도 계수) | 15.31±0.29(Predicted) |
| 물리적 상태 | 액체 |
| 비중 | 0.93 |
| 색상 | 무색의 |
| 냄새 | 100.00%에서. 꽃무늬 백합 달콤한 녹색 밀랍 열대 멜론 |
| 향취 유형 | 꽃향기 |
| 생물학적 소스 | synthetic |
| 용해도 | 35g/L at 20℃ |
| JECFA Number | 611 |
| 헨리 상수 | 9.4×102 mol/(m3Pa) at 25℃, Dupeux et al. (2022) |
| 안정성 | 공기에 민감한 |
| 주요 응용 | 향료 및 향 |
| 화장품 원료 기능 | 향수 |
| InChI | 1S/C10H20O2/c1-9(6-8-11)5-4-7-10(2,3)12/h8-9,12H,4-7H2,1-3H3 |
| InChIKey | WPFVBOQKRVRMJB-UHFFFAOYSA-N |
| SMILES | [H]C(=O)CC(C)CCCC(C)(C)O |
| LogP(분배 계수) | 1.68 at 25℃ |
| NIST | Hydroxycitronellal(107-75-5) |
| EPA | Octanal, 7-hydroxy-3,7-dimethyl- (107-75-5) |
화학적 성질
clear colourless liquid
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for < 0.1% (1 of 2046) of reports.WarningH317 (> 99.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2046 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: Octanal, 7-hydroxy-3,7-dimethyl-Hazard Traits - Fragrance AllergenOctanal, 7-hydroxy-3,7-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Octanal, 7-hydroxy-3,7-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 15-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12695Hydroxycitronellal: Does not have an individual approval but may be used under an appropriate group standard |
| 기타 안전 정보 | IMAP assessments - Octanal, 7-hydroxy-3,7-dimethyl-: Human health tier II assessment |
| 유해성 요약 | A severe eye and moderate skin irritantCauses cutaneous sensitization in 3-day intermittent dermal studies of mice[RTECS] Fragrance ingredient that is a recognized contact allergen in consumers[EC: SCCNFP] Safe when used as a flavoring agent in food[JECFA] Contained in fragrance mix[Kanerva, p. 1803] An irritant[Sigma-Aldrich MSDS] See Citronellal. |
| Hazard Classes and Categories | Skin Sens. 1 (> 99.9%)Eye irritation - category 2ASerious eye damage/eye irritation - Category 2 |
| 유해 작용 | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| 수질 위해 등급(WGK) | 1 |
| TSCA 등재 상태 | TSCA listed |
용도
개요
Hydroxycitronellal has an intense, sweet, floral, lily-type odor. It may be prepared by hydration of natural citronellal obtained from Java citronella or from Eucalyptus citriodora; P-pinene is converted to myrcene, which on hydration may yield either linalool or a mixture of geranoil and nerol; the latter mixture can be hydrogenated to citronellol and subsequently converted to citronellal and hydroxycitronellal; also by hydrogenation of 3,7-dimethyl- 7-hydroxy-2-octen-2-al over palladium carbon in ethyl acetate solution.
출처
Reported found in pepper
용도
Hydroxycitronellal is a fragrance for use in various perfumes, antiseptics, insecticides and household products; some perfumery uses (sweet pea Pois De Senteur; gardenia; cherry; melon; mint).
제조 및 합성 방법
제조 방법
The most important synthetic routes to hydroxydihydrocitronellal are listed as follows. 1) Synthesis from citronellal: One of the oldest routes to hydroxydihydrocitronellal is the hydration of the citronellal bisulfite adduct (obtained at low temperature) with sulfuric acid, followed by decomposition with sodium carbonate. A more recent development is hydration of citronellal enamines or imines, followed by hydrolysis. 2) Synthesis from citronellol. Citronellol is hydrated to 3,7-dimethyloctane-1,7- diol, for example, by reaction with 60% sulfuric acid. The diol is dehydrogenated catalytically in the vapor phase at low pressure to give highly pure hydroxydihydrocitronellal in excellent yield.The process is carried out in the presence of, for example, a copper–zinc catalyst; at atmospheric pressure, noble metal catalysts can also be used. 3) Synthesis from 7-hydroxygeranyl/-neryl dialkylamine: The starting material can be obtained by treatment of myrcene with a dialkylamine in the presence of an alkali dialkylamide, followed by hydration with sulfuric acid. The 7-hydroxygeranyl/-neryl dialkylamine isomerizes to the corresponding 7-hydroxyaldehyde enamine in the presence of a palladium(II)- phosphine complex as catalyst. Hydrolysis of the enamine gives 7-hydroxydihydrocitronellal [151].