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Levomenol

HCID 442343
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
23089-26-1
Standard-SMILES
CC(C)=CCC[C@](C)(O)[C@@H]1CC=C(C)CC1
InChIKey
RGZSQWQPBWRIAQ-CABCVRRESA-N
Summenformel
C15H26O
Durchschnittliche Molmasse
222,37 g/mol
Monoisotopische Masse
222,19836545

Überblick

(-)-alpha-Bisabolol is a sesquiterpenoid.

Namen und Bezeichner

Bevorzugter Name
Levomenol
IUPAC
(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
Lokaler Name
Levomenol
Englischer Name
(-)-alpha-bisabolol
Summenformel
C15H26O
Molmasse
222.37

Namen und Synonyme

LEVOMENOL23089-26-1(-)-alpha-Bisabololalpha-(-)-BisabololLevomenolumKamilosan1-alpha-Bisabololalpha-Bisabolol, L-DTXSID4042094alpha-Bisabolol (-)-formUNII-24WE03BX2T24WE03BX2T
Weitere Namen anzeigen
(-)-α-Bisabolol(-)-a-Bisabolol1-Methyl-4-(1,5-dimethyl-1-hydroxyhex-4(5)-enyl)cyclohexen-1CAMILLOLHYDAGEN BKamillosanDRAGOSANTOLtheta)]-thet(-)-α-BisaboL
CCRIS 9081EINECS 245-423-3Levomenolum [INN-Latin](-)-6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-olDTXCID20220943-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (alphaS,1S)-Levomenolum (INN-Latin)LEVOMENOL (MART.)

Datenbank-Bezeichner

CAS
23089-26-1
PubChem CID
442343
DTXSID
DTXSID4042094
ChEMBL

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,8
Polarare Oberfläche (TPSA)
20,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
4
Schwere Atome
16
Formalladung
0
Komplexität
284

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]
FragrancesFragrance Ingredient (alpha-Bisabolol) -> IFRA transparency List
Flavoring AgentsEU Flavoring substances
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point314.00 °C. @ 760.00 mm Hg

Physikochemische Eigenschaften

Siedepunkt
12 · bp12 153°
Dichte
20 · d20 0.9211
Dampfdruck
0.015 Pa · 0.015Pa at 20℃
Brechungsindex
20 · n20/D 1.496
FEMA
4666 · 4666 | ALPHA-BISABOLOL
Flammpunkt
135 °C · 135 °C

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 3% (12 of 401) of reports.

Warning

H317 (18.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 401 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: 3-Cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-pentenyl)-, [S-(R*,R*)]-

Status: Active Update: 09-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/23596

Alpha-(-)-bisabolol: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Sens. 1 (18.7%)

Sicherheitsdaten

wgk
3
ridadr
UN 3082 9 / PGIII
hs_code
2906195000
RTECS-Nr.
MJ9685000
Toxizität
LD50 in male, female mice, rats (ml/kg): 15.2, 15.0, 14.9, 15.6 orally (Habersang)
Speicherklasse
10 - Combustible liquids
Hazard Classifications
Aquatic Chronic 3

Chemie und Industrie

Pharmakologische Informationen

PharmacodynamicsLevomenol is an anti-inflammatory and natural moisturizing agent that has been found to diminish the signs of photodamage, reduce pruritus, and ameliorate skin texture and elasticity.
Absorption, Distribution and Excretion · 2 Einträge

The purpose of the present investigations was to study the cutaneous absorption of sesquiterpenic alcohol, the major active principle of chamomile. For these investigations 14C-labelled levomenol ((-)-6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol; (-)-alpha-bisabolol) was prepared by biochemical incorporation of [14C]-acetate into the molecule. 5 h after topical application of the radiolabelled substance onto nude mice half of the radioactivity was found in the skin. The other part was measured in tissue and organes. 90% of this radioactivity was analysed as intact levomenol.

To demonstrate the distribution of the substance in the skin a part of this tissue was cutted into horizontal slices by a cryotome. From the slices autoradiograms were produced. The densitometric measuration showed that there was a fast penetration of levomenol into the skin. 5 h after the topical application the substance was displaced from outermost to innermost areas. From these results a fast cutaneous absorption and a long therapeutical effect of the antiphlogistic and spasmolytic levomenol in the skin can be expected.

Cellular LocationsExtracellular

Verwendung und Herstellung

IFRA Fragrance Standards · 6 Einträge

alpha-Bisabolol

(R*,R*)-.α.,4-Dimethyl-.α.-(4-methyl-3-pentenyl)cyclohex-3-ene-1-methanol; 3-Cyclohexene-1-methanol, .α.,4-dimethyl-.α.-(4-methyl-3-pentenyl)-, (R*,R*)-; 6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol; 3-Cyclohexene-1-methanol, α,4-dimethyl-α-(4-methyl-3-penten-1- yl)-; 3-Cyclohexene-1-methanol, α,4-dimethyl-α-(4-methyl-3-penten-1- yl)-, (αS,1S)-; 3-Cyclohexene-1-methanol, α,4-dimethyl-α-(4-methyl-3-penten-1- yl)-, (αR,1R)-; 3-Cyclohexene-1-methanol, α,4-dimethyl-α-(4-methyl-3-penten-1- yl)-, (αR,1S)-; 3-Cyclohexene-1-methanol, α,4-dimethyl-α-(4-methyl-3-penten-1- yl)-, (αS,1R)-; alpha-Bisabolol; Bisabolol; Bisabolol nat. roh (Candela-Öl) (Commercial name); Dragosantol (Commercial name)

Zugehörige Reaktionen

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Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 1706937
HRID 1706937als Eduktuspto-grants-1980_06

Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
CHEMBL1096927
ChEBI
CHEBI:125
UNII
24WE03BX2T
EC Number
245-423-3
Nikkaji
J38.588C
storage temp.
-20 °C · -20°C
Löslichkeit
100 · DMSO:100.0(Max Conc. mg/mL);449.7(Max Conc. mM)
Aggregatzustand
Liquid
pka
15.04 · 15.04±0.29(Predicted)
Farbe
Colorless to light yellow
Geruch (Odor)
100 % · at 100.00 %. fruity nutty coconut
Geruchsart
floral
Wasserlöslichkeit
22 mg/L · 22mg/L at 20℃
JECFA Number
2031 · 2031
Kosmetik-Inhaltsstoffe Funktionen
SKIN CONDITIONINGSOOTHINGFRAGRANCE
InChI
1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1
InChIKey
RGZSQWQPBWRIAQ-CABCVRRESA-N
SMILES
O[C@]([C@H]1CCC(=CC1)C)(CCC=C(C)C)C
LogP
5.5 at · 5.5 at 25℃
CAS Datenbank
23089 · 23089-26-1(CAS DataBase Reference)
EPA chemische Informationen
Levomenol (23089-26-1)

IFRA_STD_192.pdf

49

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

Use Classification · 2 Einträge

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Restriction Limits in the Finished Product (%) · 6 Einträge

0.42 [Products applied to the lips]

0.13 [Products applied to the axillae]

2.5 [Products applied to the face/body using fingertips]

2.4 [Products related to fine fragrances]

0.6 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]

0.6 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]

Anwendungen

Verwenden(-)-α-Bisabolol was used to investigate the leishmanicidal and cytotoxic activity of essential oil of Vanillosmopsis arborea.

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