(S)-p-Mentha-1,8-dien

Limonene, (-)-

HCID 439250CAS 5989-54-8
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Grundinformationen

Standard-SMILES
C=C(C)[C@@H]1CC=C(C)CC1
InChIKey
XMGQYMWWDOXHJM-SNVBAGLBSA-N
Summenformel
C10H16
Durchschnittliche Molmasse
136,23 g/mol
Monoisotopische Masse
136,12520051

Überblick

(4S)-limonene is an optically active form of limonene having (4S)-configuration. It is an enantiomer of a (4R)-limonene.

Namen und Bezeichner

Bevorzugter Name
Limonene, (-)-
IUPAC
(4S)-1-methyl-4-prop-1-en-2-ylcyclohexene
Lokaler Name
(S)-p-Mentha-1,8-dien
Englischer Name
(S)-(-)-Limonene
Summenformel
C10H16
Molmasse
136.23

Namen und Synonyme

(-)-Limonenel-Limonenebeta-LimoneneLimonene, (-)-Limonene, L-P-Mentha-1,8-diene, (S)-(-)-UNII-47MAJ1Y2NE47MAJ1Y2NECyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-EINECS 227-815-6AI3-25390EC 227-815-6
Weitere Namen anzeigen
(-)-Dipentene(s)-(-)-p-mentha-8-diene(-)-1,8-p-menthadiene,(S)-(-)-limonene(S)-(-)-4-ISOPROPENYL-1-METHYL-1-CYCLOHEXENE1-methyl-4-(1-methylethenyl)-,(S)-Cyclohexenecyclohexene,1-methyl-4-(1-methylethenyl)-,(S)-
1-Methyl-4-(1-methylethenyl)cyclohexene, (S)-RefChem:41455227-815-65989-54-8(S)-(-)-Limonene(S)-Limonene(S)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene(-)-(4S)-Limonene

Datenbank-Bezeichner

CAS
5989-54-8
PubChem CID
439250
DTXSID
DTXSID6047078
ChEMBL
CHEMBL236688
ChEBI
CHEBI:15383
UNII
47MAJ1Y2NE
EC Number
227-815-6
Nikkaji
J85.992C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,4
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
1
Schwere Atome
10

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Terpenes
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
CosmeticsCosmetics ingredient -> Base; Colorant; Conditioning/Emollient; Emulsifier; Flavor; Fragrance; Moisturizing/Humectant; Opacifying Agent; Other (Specify); Preservative/Stabilizer; Solvent
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (l-Limonene) -> IFRA transparency List
LogP4.57

Physikochemische Eigenschaften

Schmelzpunkt
-74 °C · -74°C
Siedepunkt
175 · 175-177 °C(lit.)
Dichte
0.844 g/mL · 0.844 g/mL at 25 °C(lit.)
Dampfdichte
4.7 · 4.7 (vs air)
Dampfdruck
3 mm · <3 mm Hg ( 14.4 °C)
Brechungsindex
20 · n20/D 1.471(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P302+P352, P303+P361+P353, P321, P332+P317, P333+P317, P362+P364, P370+P378, P391, P403+P235, and P501 (click each P-code to see the statement)

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P321, P331, P332+P317, P333+P317, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 28-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/10807

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

Other Safety InformationPEC / SN / Other assessments - Limonene: Health and Environment
Hazards Summary · 1 Eintrag

A skin sensitizer; A mild skin, eye, and respiratory tract irritant; [CHEMINFO] Danger of skin sensitization; [MAK] An irritant; May cause skin sensitization; Effects in high-dose animal studies include acute tubular necrosis; [MSDSonline] The racemic mixture of d-limonene and l-limonene is called dipentene or limonene (138-86-3). [Kanerva, p. 1789] See Limonene and d-Limonene.

Hazard Classes and Categories · 3 Einträge

Flam. Liq. 3 (100%)

Flammable liquid - category 3

Flam. Liq. 3

Toxikologische Informationen

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.

Sicherheitsdaten

F
8-10-23
wgk
2
tsca
TSCA listed
ridadr
UN 2052 3/PG 3
hs_code
29029090
RTECS-Nr.
OS8350000

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites(-)-limonene has known human metabolites that include Carveol and Perillyl alcohol.
Cellular LocationsExtracellular

Verwendung und Herstellung

Uses · 2 Einträge

Used in artificial essential oils and to make (+)-carvone; Occurs naturally in essential oils of pine, peppermint, spearmint, and other plants; A minor constituent of turpentine; [CHEMINFO] Used in flavorings, fragrances, cosmetics and as a solvent and wetting agent; Also used to make resins, insecticides, insect repellants, and animal repellants; [HSDB]

Painting (Solvents) [Category: Paint]

Household Products · 2 Einträge

Cosmetics product ingredient: Limonene (1-methyl-4-prop-1-en-2-yl-cyclohexene; dl-limonene (racemic); Dipentene; (R)-p-mentha-1,8-diene; (d-limonene); (S)-p-mentha-1,8-diene; (l-limonene))

Information on 16 consumer products that contain L-Limonene in the following categories is provided:

Use ClassificationFragrance Ingredients
General Manufacturing InformationCyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-: ACTIVE
Anwendungen · 3 Einträge

Beschreibungι-Limonene has a pleasant, lemon-like odor free from camphora ceous and turpentine-like notes. The most important and wide spread terpene; it is known in the d- and ι- optically active forms and in the optically inactive dl-form (known as dipentene); it has been reported found in more than 300 essential oils in amounts ranging from 90 - 95% (lemon, orange, mandarin) to as low as 1% (palmarosa);1 the most widespread form is the d-limonene, followed by the racemic form, and then ι-limonene.

OccurrenceIt has been reported found in more than 300 essential oils in amounts ranging from 90 to 95% (lemon, orange, mandarin) to as low as 1% (palmarosa); the most widespread form is the d-limonene, followed by the racemic form and then l-limo nene. Also reported found in ginger, nutmeg, pepper, mace, hop oil, coriander seed, calamus, dill herb, caraway seed and rosemary.

Verwenden(S)-(-)-Limonene is used to inhibit the proliferation of colon cancer cells. It is also used in artificial essential oils in order to produce (+)-carvone. It is an active component of turpentine. Further, it is used in flavorings, fragrances, and cosmetics. It finds application as a solvent and wetting agent. In addition to this it is used to produce resins.

Darstellung

synthetisched-Limonene may be obtained by steam distillation of citrus peels and pulp resulting from the production of juice and cold pressed oils, or from deterpenation of citrus oils; it is sometimes redistilled.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: An optically active form of limonene having (4S)-configuration.

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