CAS 50373-36-9 (-)-Isopulegol (HCID 170833)

概要

Isopulegol is a p-menthane monoterpenoid. It has a role as a metabolite.

名称と識別子

優先名称: (-)-Isopulegol
IUPAC: (1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
現地名: (1R,3R,4S)-1β-メチル-4α-イソプロペニルシクロヘキサン-3β-オール
英語名: ISOPULEGOL
分子式: C10H18O
分子量: 154.25

名称と別名

(-)-IsopulegolIsopulegol89-79-2l-Isopulegolcoolact P(1R,2S,5R)-5-METHYL-2-(PROP-1-EN-2-YL)CYCLOHEXAN-1-OLFEMA No. 29623TH92O3BXN(1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-olNSC-231369DTXSID5047116RefChem:792269

名称をさらに表示

(1R,2S,5R)-2-イソプロペニル-5-メチルシクロヘキサノール(1R,3R,4S)-1β-メチル-4α-イソプロペニルシクロヘキサン-3β-オール(-)-イソプレゴールイソプレゴール8-p-メンテン-3-オール(1R)-2α-(1-メチルエテニル)-5β-メチルシクロヘキサン-1β-オール(1R)-5β-メチル-2α-(1-メチルエテニル)シクロヘキサノール(1R,2S,5R)-2-イソプロペニル-5-メチル-1-シクロヘキサノール(1R)-5β-メチル-2α-(1-メチルエテニル)-1β-シクロヘキサノール(1R,3R,4S)-イソプレゴールl-イソプレゴール(1R)-2α-イソプロペニル-5β-メチルシクロヘキサン-1β-オール(1R,4S,3R)-p-メンタ-8-エン-3β-オール(1β)-2α-イソプロペニル-5β-メチルシクロヘキサノールiso-プレゴール(1R,1β,4α)-p-メンタ-8-エン-3β-オール2α-(1-メチルエテニル)-5β-メチルシクロヘキサン-1β-オールイソプレゴール, (-)-(−)-イソプレゴールDL-ISOPULEGOL(?)-IsopulegolFEMA 2962(-)-Isopulegol 99%ISOPULEGOL 99+%ISOPULEGOL, (-)-

DTXCID501764296201-940-6p-Menth-8-en-3-ol50373-36-9Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-(-)-L-Isopulegol(1R,2S,5R)-2-Isopropenyl-5-methylcyclohexanolNVG8YK55NL

データベース識別子

CAS: 50373-36-9、59905-53-2、89-79-2
PubChem CID: 170833
DTXSID: DTXSID5047116
ChEMBL: CHEMBL237994
ChEBI: CHEBI:70479
UNII: 3TH92O3BXN、NVG8YK55NL
EC Number: 201-940-6、256-557-7
Nikkaji: J3.215H

物性

構造計算による物性

XLogP: 3
極性表面積: 20.2 Å²
水素結合供与体数: 1
水素結合受容体数: 1
回転可能結合数: 1
重原子数: 11
形式電荷: 0
複雑度: 151

実験および物理化学的性質

FragrancesFragrance Ingredient (Isopulegol) -> IFRA transparency List

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Density0.904-0.913

Flavoring AgentsEU Flavoring substances

Solubility · 2 件

slightly soluble in water; soluble in oils

miscible (in ethanol)

Boiling Point · 2 件

216.00 to 218.00 °C. @ 760.00 mm Hg

218 °C

物理化学的性質

融点: 78 °C · 78°C
沸点: 212 °C · 212 °C(lit.)
比重(密度): 0.912 g/mL · 0.912 g/mL at 25 °C(lit.)
蒸気圧: 13.97 Pa · 13.97Pa at 20℃
屈折率: 20 · n20/D 1.471(lit.)
FEMA: 2962 · 2962 | ISOPULEGOL
闪点: 195 °F · 195 °F
貯蔵温度: -20 °C · -20°C
溶解性: クロロホルム（微量）、メタノール（微量）
酸解離定数(Pka): 15.11 · 15.11±0.60(Predicted)
外見: Liquid
色: 無色
臭い (Odor): 10 %。ミント · ジプロピレングリコール中10.00%。ミントクーリングメディカルウッディ
においのタイプ: ミント系
由来生物: synthetic
水溶解度: 3 g/L · 3g/L at 21.9℃
JECFA Number: 755 · 755
BRN: 1906573 · 1906573
安定性: Light sensitive
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/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
InChIKey: ZYTMANIQRDEHIO-KXUCPTDWSA-N
SMILES: C[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C
LogP: 2.4 at · 2.4 at 23℃
CAS データベース: 89 · 89-79-2(CAS DataBase Reference)
EPAの化学物質情報: Isopulegol (89-79-2)

化学的性質

化学的特性Isopulegol is a cyclic nonaromatic alcohol.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1823) of reports.

Warning

H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1823 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危険有害性情報

Regulatory Information · 5 件

Chemical: Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, [1R-(1.alpha.,2.beta.,5.alpha.)]-

Regulation (EC) No 1831/2003 (amended)

Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)- 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: 16-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11447

Isopulegol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Pulegone and related substances: Human health tier II assessment

Hazard Classes and Categories · 3 件

Acute Tox. 4 (> 99.9%)

Flam. Liq. 3 (100%)

Carcinogenicity - category 2

安全データ

F: 10-23
wgk: 2
tsca: TSCA listed
ridadr: NA 1993 / PGIII
毒性: The acute oral LD50 in rats was reported as 1.03 ± 0.10 ml/kg and the acute dermal LD50 in rabbits as approximately 3 ml/kg
risk_code: 22-36/37/38
hazard_code: Xn
safety_code: 26-36/37/39
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス: 10 - Combustible liquids

化学と産業

薬理情報

Cellular LocationsExtracellular

用途と製造

U.S. Production2023: 15,884 lb

Consumer UsesOther

Industry UsesFragrance

Household Products · 2 件

Information on 2 consumer products that contain Isopulegol in the following categories is provided:

Information on 1 consumer products that contain Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-rel- in the following categories is provided:

Use Classification · 3 件

Fragrance Ingredients

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 3 件

Other (requires additional information)

Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-: ACTIVE

Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-rel-: ACTIVE

応用分野 · 4 件

説明Synthesis: Several stereoisomers are possible; only l-isopulegol and d-α-isopulegol have been isolated from mixtures of alcohols obtained by cyclization of d-citronellal.

天然物の起源l-Isopulegol has been reported found in the essences of lemongrass, East African geranium and Eucalyptus citriodora; d-isopulegol is present in the oils of Backhousia and Baeckea citriodorae; d-neoisopulegol is found in Mentha rotundifolia. Also reported found in mint, mandarin, orange juice, citrus peel oils, currant bud, ginger, corn mint oil, cognac, rum, buchu oil, lemon balm and mastic gum oil

使用isopulegol is used in perfume compositions as a "lift" to Rose notes, Geranium notes, Reseda and Oriental types, various floral fragrances, including Tuberose, etc. It is also used in flavor compositions in concentrations equal to 5 to 30 ppm in the finished product. The application is mainly in the minty types and in a few Berry flavor types.

一般的な説明Isopulegol is monoterpene alcohol, a useful ingredient for the production of fragrances in perfume industries. It is also used as a starting material in the manufacture of menthol by the hydrogenation process. Menthol is an important component in cosmetics, pharmaceuticals, and toothpaste.

調製方法

製造方法Several stereoisomers are possible; only l-isopulegol and d-α-isopulegol have been isolated from mixtures of alcohols obtained by cyclization of d-citronellal.