기본 정보
- 표준 SMILES
CC(CC=O)CCCC(C)(C)O- InChIKey
WPFVBOQKRVRMJB-UHFFFAOYSA-N- 분자식
- C10H20O2
- 평균 분자량
- 172.26 g/mol
- 단동위원소 질량
- 172.14632988
개요
Hydroxycitronellal is the tertiary alcohol arising from addition of water across the C=C double bond of citronellal. It has a role as a fragrance and an allergen. It is functionally related to a citronellal.
이름 및 식별자
- 우선 이름
- Hydroxycitronellal
- IUPAC
- 7-hydroxy-3,7-dimethyloctanal
- 현지명
- 하이드록시시트로넬랄
- 영어명
- 3,7-Dimethyl-7-hydroxyoctanal
- 분자식
- C10H20O2
- 분자량
- 172.26
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
107-75-5- PubChem CID
- 7888
- DTXSID
DTXSID6042232- ChEMBL
CHEMBL3186027- ChEBI
CHEBI:53459- UNII
- 8SQ0VA4YUR
- EC Number
- 203-518-7
- Nikkaji
- J2.859B
물성
구조 계산 물성
- XLogP
- 1.6
- 극성 표면적
- 37.3 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 12
- 형식 전하
- 0
- 복잡도
- 130
실험 및 물리화학적 성질
Cosmetics
Cosmetics ingredient -> Base; Flavor; Fragrance; Moisturizing/Humectant; Other (Specify)
Masking
Solubility
slightly
slightly soluble in water; soluble in alcohol, propylene glycol, and oils; insoluble in glycerol
1 ml in 1 ml 50% alcohol (in ethanol)
Boiling Point
241.00 °C. @ 760.00 mm Hg
241 °C; 94-96 °C (1 mm Hg)
Physical Description
Liquid; Dry Powder; Liquid; CBI
Liquid; [Sigma-Aldrich MSDS]
colourless liquid with sweet floral lily-like odour
물리화학적 성질
- 녹는점
- 22 · 22-23 °C
- 끓는 점
- 257 °C · 257 °C(lit.)
- 밀도
- 0.923 g/mL · 0.923 g/mL at 25 °C(lit.)
- 증기압
- 0.547 Pa · 0.547Pa at 20℃
- FEMA
- 2583 · 2583 | HYDROXYCITRONELLAL
- 굴절률
- 20 · n20/D 1.448(lit.)
- 인화점
- 230 °F · >230 °F
- 저장 조건
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- 용해도
- 벤젠(약간 용해됨), 클로로포름(약간 용해됨), 메탄올(약간 용해됨)
- 산도 계수 (pKa)
- 15.31 · 15.31±0.29(Predicted)
- 물리적 상태
- 액체
- Specific Gravity
- 0.93 · 0.93
- 색상
- 무색의
- 냄새
- 100 %에서 · 100.00%에서. 꽃무늬 백합 달콤한 녹색 밀랍 열대 멜론
- 냄새 유형
- 꽃향기
- 생물학적 소스
- synthetic
- 수용성
- 35 g/L · 35g/L at 20℃
- JECFA Number
- 611 · 611
- Henry's Law Constant
- 9.4 · 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
- 1.68 at · 1.68 at 25℃
- NIST
- Hydroxycitronellal(107-75-5)
- EPA
- 7 · Octanal, 7-hydroxy-3,7-dimethyl- (107-75-5)
화학적 성질
clear colourless liquid
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 2046) of reports.
Warning
H317 (> 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.
Warning
유해성 정보
Regulatory Information
Chemical: Octanal, 7-hydroxy-3,7-dimethyl-
Hazard Traits - Fragrance Allergen
Octanal, 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/12695
Hydroxycitronellal: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
A severe eye and moderate skin irritant; Causes 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 2A
Serious eye damage/eye irritation - Category 2
독성 정보
안전 데이터
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- RG7850000
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- HS 번호
- 29124990
- risk_code
- 38-41-43
- hazard_code
- Xi
- safety_code
- 26-39-36/37
- 기존화학 물질
- KE-20434
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2Skin Sens. 1
- 스토리지 클래스
- 10 - Combustible liquids
화학 및 산업
약리 정보
Metabolism/Metabolites
Studies in rabbits have shown that hydroxycitronellal is converted to two primary metabolites: reduction to the alcohol 7-hydroxycitronellol and oxidation to the carboxylic acid 7-hydroxycitronellylic acid. On average, about 50% of hydroxycitronellal is excreted as 7-hydroxycitronellylic acid which is therefore regarded as the major metabolite.
FDA Pharmacological Classification
8SQ0VA4YUR
HYDROXYCITRONELLAL
Established Pharmacologic Class [EPC] - Standardized Chemical Allergen
Physiologic Effects [PE] - Increased Histamine Release
Physiologic Effects [PE] - Cell-mediated Immunity
Chemical Structure [CS] - Allergens
용도 및 제조
IFRA Fragrance Standards
Hydroxycitronellal
Hydroxycitronellal; Citronellalhydrate; 7-Hydroxy-3,7-dimethyloctanal; 3,7-Dimethyl-7-hydroxyoctanal; Octanal, 7-hydroxy-3,7-dimethyl-; Oxydihydrocitronellal; Laurinal (commercial name); Laurine (commercial name)
IFRA_STD_043.pdf
51
IFRA 51st Amendment - Guidance for the use of IFRA Standards
Restriction: This material should be used only in the limited quantity as stated in the Standard
Household Products
Cosmetics product ingredient: Hydroxycitronellal (7-Hydroxycitronellal)
Information on 159 consumer products that contain Hydroxycitronellal in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
Octanal, 7-hydroxy-3,7-dimethyl-: ACTIVE
Restriction Limits in the Finished Product (%)
0.38 [Products applied to the lips]
0.11 [Products applied to the axillae]
2.2999999999999998 [Products applied to the face/body using fingertips]
2.1 [Products related to fine fragrances]
0.53 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]
0.53 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]
응용 분야
개요Hydroxycitronellal 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.
출처Reported found in pepper
용도Hydroxycitronellal 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 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].
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
추가 설명
순도시험(1) 비중 : 이 품목의 비중은 0.918~0.923이어야 한다. (2) 굴절률 : 이 품목의 굴절률 은 1.447~1.450이어야 한다. (3) 용상 : 이 품목 1mL를 50% 에탄올 1mL에 녹일 때, 그 액은 징명하여야 한다. (4) 산가 : 이 품목의 산가는 향료시험법 중 산가측정법에 따라 시험할 때, 5 이하이어야 한다.
순도시험(1) 비중 : 이 품목의 비중은 0.925~0.930이어야 한다. (2) 굴절률 : 이 품목의 굴절률 은 1.441~1.444이어야 한다. (3) 용상 : 이 품목 1mL를 50% 에탄올 2mL에 녹일 때, 그 액은 징명하여야 한다. (4) 산가 : 이 품목의 산가는 향료시험법 중 산가측정법에 따라 시험할 때, 1 이하이어야 한다. (5) 히드록시시트로넬랄 : 이 품목 약 5g을 정밀히 취해 향료시험법 중 알데히드류 및 케톤류함량측정법의 히드록실아민법 중 제2법에 따라 시험할 때, 검체 1g에 대응하는 0.5N 염산의 소비량은 3% 이하이어야 한다. 다만, 방치시간은 1시간으로 한다.
확인시험이 품목 1mL에 아황산수소나트륨시액 5mL를 넣어 흔들어 섞으면 발열하며 녹고 냉각하면 결정성덩어리로 된다.
확인시험이 품목 1mL에 에탄올 1mL 및 0.5N 황산 1mL를 넣어 수욕 중에서 흔들어 섞으면서 약 3분간 가열하면 특이한 향기를 발생한다.
정량법이 품목 약 1.5g을 정밀히 달아 향료시험법 중 알데히드류 및 케톤류함량측정법의 히드록실아민법 중 제1법에 따라 시험하고 다음 계산식에 따라 함량을 구한다. 다만, 가열시간은 5분간으로 한다.a : 검체 1g에 대응하는 0.5N 알콜성수산화칼륨용액의 소비량(mL)b : 순도시험 (5)에서 얻은 0.5N 염산의 소비량(mL)
정량법이 품목 약 1g을 정밀히 달아 향료시험법 중 알데히드류 및 케톤류함량측정법의 히드록실아민법 중 제2법에 따라 시험한다. 다만, 방치시간은 1시간으로 한다.0.5N 염산 1mL = 86.13mg C10H20O2
정의ChEBI: The tertiary alcohol arising from addition of water across the C2C double bond of citronellal.
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