Isopulegol

(-)-Isopulegol

HCID 170833CAS 50373-36-9
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Grundinformationen

Standard-SMILES
C=C(C)[C@@H]1CC[C@@H](C)C[C@H]1O
InChIKey
ZYTMANIQRDEHIO-KXUCPTDWSA-N
Summenformel
C10H18O
Durchschnittliche Molmasse
154,25 g/mol

Überblick

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

Namen und Bezeichner

Bevorzugter Name
(-)-Isopulegol
IUPAC
(1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
Lokaler Name
Isopulegol
Englischer Name
ISOPULEGOL
Summenformel
C10H18O
Molmasse
154.25

Namen und Synonyme

(-)-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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3
Polarare Oberfläche (TPSA)
20,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
1
Schwere Atome
11

Experimentelle und physikochemische Eigenschaften

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 Einträge

slightly soluble in water; soluble in oils

miscible (in ethanol)

Boiling Point · 2 Einträge

216.00 to 218.00 °C. @ 760.00 mm Hg

218 °C

Physikochemische Eigenschaften

Schmelzpunkt
78 °C · 78°C
Siedepunkt
212 °C · 212 °C(lit.)
Dichte
0.912 g/mL · 0.912 g/mL at 25 °C(lit.)
Dampfdruck
13.97 Pa · 13.97Pa at 20℃
Brechungsindex
20 · n20/D 1.471(lit.)
FEMA
2962 · 2962 | ISOPULEGOL

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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

Gefahrenhinweise

Regulatory Information · 5 Einträge

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 Einträge

Acute Tox. 4 (> 99.9%)

Flam. Liq. 3 (100%)

Carcinogenicity - category 2

Sicherheitsdaten

F
10-23
wgk
2
tsca
TSCA listed
ridadr
NA 1993 / PGIII
risk_code
22-36/37/38
Toxizität
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

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsExtracellular

Verwendung und Herstellung

U.S. Production2023: 15,884 lb
Consumer UsesOther
Industry UsesFragrance
Household Products · 2 Einträge

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 Einträge

Fragrance Ingredients

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 3 Einträge

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

Anwendungen · 3 Einträge

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

Occurrencel-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

Verwendenisopulegol 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.

Darstellung

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

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A natural product found in Citrus hystrix.

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