基本情報
- 標準SMILES
CC(CC=O)CCCC(C)(C)O- InChIKey
WPFVBOQKRVRMJB-UHFFFAOYSA-N- 分子式
- C10H20O2
- 平均分子量
- 172.26 g/mol
- 単同位体質量
- 172.14632988
概要
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.
名称と識別子
- 優先名称
- Hydroxycitronellal
- IUPAC
- 7-hydroxy-3,7-dimethyloctanal
- 現地名
- [R,(+)]-7-ヒドロキシ-3,7-ジメチルオクタナール
- 英語名
- 3,7-Dimethyl-7-hydroxyoctanal
- 分子式
- C10H20O2
- 分子量
- 172.26
名称と別名
名称をさらに表示
データベース識別子
- CAS
107-75-5- PubChem CID
- 7888
- DTXSID
DTXSID6042232- ChEMBL
CHEMBL3186027- ChEBI
CHEBI:53459- UNII
- 8SQ0VA4YUR
- EC Number
- 203-518-7
- Nikkaji
- J2.859B
物性
構造計算による物性
- XLogP
- 1.6
- 極性表面積
- 37.3 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 2
- 回転可能結合数
- 6
- 重原子数
- 12
- 形式電荷
- 0
- 複雑度
- 130
実験および物理化学的性質
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
物理化学的性質
- 融点
- 22 · 22-23 °C
- 沸点
- 257 °C · 257 °C(lit.)
- 比重(密度)
- 0.923 g/mL · 0.923 g/mL at 25 °C(lit.)
- 蒸気圧
- 0.547 Pa · 0.547Pa at 20℃
- FEMA
- 2583 · 2583 | HYDROXYCITRONELLAL
- 屈折率
- 20 · n20/D 1.448(lit.)
- 闪点
- 230 °F · >230 °F
- 貯蔵温度
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- 溶解性
- ベンゼン(微量)、クロロホルム(微量)、メタノール(微量)
- 酸解離定数(Pka)
- 15.31 · 15.31±0.29(Predicted)
- 外見
- 液体
- 比重
- 0.93 · 0.93
- 色
- 無色透明
- 臭い (Odor)
- 100 %で。花のユリ、甘い緑のワックス状のトロピカル · 100.00%で。花のユリ、甘い緑のワックス状のトロピカル メロン
- においのタイプ
- 花柄
- 由来生物
- synthetic
- 水溶解度
- 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)
- 安定性
- 空気に敏感
- 主な用途
- フレーバーそして香料
- 化粧品成分の機能
- 香料
- 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℃
- CAS データベース
- 107 · 107-75-5(CAS DataBase Reference)
- NISTの化学物質情報
- Hydroxycitronellal(107-75-5)
- EPAの化学物質情報
- 7 · Octanal, 7-hydroxy-3,7-dimethyl- (107-75-5)
化学的性質
化学的特性clear colourless liquid
安全と法規制
GHS分類
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
危険有害性情報
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
毒性情報
安全データ
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- RG7850000
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- hs_code
- 29124990
- risk_code
- 38-41-43
- 消防法
- 危-4-3-III
- hazard_code
- Xi
- safety_code
- 26-39-36/37
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2Skin Sens. 1
- ストレージクラス
- 10 - Combustible liquids
化学と産業
薬理情報
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
用途と製造
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)]
応用分野
用途スズラン、ユリ、ボダイジュ花、ライラック、シクラメン様香料の調合剤。
説明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.
天然物の起源Reported found in pepper
使用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).
調製方法
製造方法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].
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義本品は、次の化学式で表されるテルペンアルデヒドである。
定義ChEBI: The tertiary alcohol arising from addition of water across the C2C double bond of citronellal.
関連反応
関連ノート
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