(-)-Isopulegol (HCID 170833)

개요

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

이름 및 식별자

우선 이름: (-)-Isopulegol
IUPAC: (1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
현지명: 아이소푸레골
영어명: ISOPULEGOL
분자식: C10H18O
분자량: 154.25

이름 및 동의어

(-)-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

이름 더 보기

아이소푸레골아이소풀렉올DL-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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: 3
극성 표면적: 20.2 Å²
수소 결합 공여자 수: 1
수소 결합 수용자 수: 1
회전 가능 결합 수: 1
무거운 원자 수: 11
형식 전하: 0
복잡도: 151

실험 및 물리화학적 성질

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 · 2건

slightly soluble in water; soluble in oils

miscible (in ethanol)

Boiling Point · 2건

216.00 to 218.00 °C. @ 760.00 mm Hg

218 °C

물리화학적 성질

녹는점: 78 °C · 78°C
끓는 점: 212 °C · 212 °C(lit.)
밀도: 0.912 g/mL · 0.912 g/mL at 25 °C(lit.)
증기압: 13.97 Pa · 13.97Pa at 20℃
굴절률: 20 · n20/D 1.471(lit.)
FEMA: 2962 · 2962 | ISOPULEGOL
인화점: 195 °F · 195 °F
저장 조건: -20 °C · -20°C
용해도: 클로로포름(약간 용해됨), 메탄올(약간 용해됨)
산도 계수 (pKa): 15.11 · 15.11±0.60(Predicted)
물리적 상태: Liquid
색상: 무색
냄새: 10 % · 디프로필렌 글리콜 중 10.00%. 민트티 쿨링 약용 우디
냄새 유형: 민트 맛
생물학적 소스: synthetic
수용성: 3 g/L · 3g/L at 21.9℃
JECFA Number: 755 · 755
BRN: 1906573 · 1906573
안정성: 감광성
주요 응용: 향료 및 향
화장품 원료 기능: 향기
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℃
EPA: Isopulegol (89-79-2)

화학적 성질

Isopulegol is a cyclic nonaromatic alcohol.

안전 및 규제

GHS 분류

GHS Classification · 6건

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

유해성 정보

Regulatory Information · 5건

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 · 3건

Acute Tox. 4 (> 99.9%)

Flam. Liq. 3 (100%)

Carcinogenicity - category 2

안전 데이터

wgk: 2
tsca: TSCA listed
ridadr: NA 1993 / PGIII
독성: 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
기존화학 물질: 2003-3-2347
F 고인화성물질: 10-23
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
스토리지 클래스: 10 - Combustible liquids

화학 및 산업

약리 정보

Cellular LocationsExtracellular

용도 및 제조

U.S. Production2023: 15,884 lb

Consumer UsesOther

Industry UsesFragrance

Household Products · 2건

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 · 3건

Fragrance Ingredients

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 3건

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

응용 분야 · 4건

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

출처l-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

용도isopulegol 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.

일반 설명Isopulegol 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.

제조 방법

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