(-)-リモネン

Limonene, (-)-

HCID 439250CAS 5989-54-8
部分構造検索類似構造を探す

基本情報

標準SMILES
C=C(C)[C@@H]1CC=C(C)CC1
InChIKey
XMGQYMWWDOXHJM-SNVBAGLBSA-N
分子式
C10H16
平均分子量
136.23 g/mol
単同位体質量
136.12520051

概要

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

名称と識別子

優先名称
Limonene, (-)-
IUPAC
(4S)-1-methyl-4-prop-1-en-2-ylcyclohexene
現地名
(-)-リモネン
英語名
(S)-(-)-Limonene
分子式
C10H16
分子量
136.23

名称と別名

(-)-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
名称をさらに表示
(-)-リモネンl-リモネン1-メチル-4β-イソプロペニル-1-シクロヘキセン[S,(-)]-p-メンタ-1,8-ジエン(S)-4-イソプロペニル-1-メチル-1-シクロヘキセン(S)-リモネン(S)-(-)-リモネン1-メチル-4β-(1-メチルエテニル)シクロヘキセン[S,(-)]-1-メチル-4-(1-メチルエテニル)シクロヘキセン1-メチル-4β-イソプロペニルシクロヘキセン(-)-(4S)-リモネン(4S)-p-メンタ-1(6),8-ジエン(4S)-1-メチル-4β-イソプロペニル-1-シクロヘキセン(4S)-1-メチル-4-イソプロペニル-1-シクロヘキセン(S)-1-メチル-4-イソプロペニル-1-シクロヘキセンβ-リモネン(4S)-1-メチル-4β-(1-メチルエテニル)-1-シクロヘキセン(-)-p-メンタン-1,8-ジエン（S）-4-イソプロペニル-1-メチルシクロヘキサ-1-エン(S)‐(-)‐リモネン(-)-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

データベース識別子

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

物性

構造計算による物性

XLogP
3.4
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
1
重原子数
10

実験および物理化学的性質

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

物理化学的性質

融点
-74 °C · -74°C
沸点
175 · 175-177 °C(lit.)
比旋光度
-99.5 · -99.5 º (C=NEAT)
比重(密度)
0.844 g/mL · 0.844 g/mL at 25 °C(lit.)
蒸気密度
4.7 · 4.7 (vs air)
蒸気圧
3 mm · <3 mm Hg ( 14.4 °C)

化学的性質

化学的特性colourless liquid with lemon odour

安全と法規制

GHS分類

GHS Classification · 6 件

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)

危険有害性情報

Regulatory Information · 4 件

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 件

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 件

Flam. Liq. 3 (100%)

Flammable liquid - category 3

Flam. Liq. 3

毒性情報

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

安全データ

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

化学と産業

薬理情報

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

用途と製造

Uses · 2 件

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 件

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
応用分野 · 6 件

用途香料原料。

用途その炭化水素系の物質（ゴムやプラスチック）に対しての溶剤としての特性を活かした利用法が開拓されている。かつては洗剤の汚れ落とし成分に多用されてきたが、現在ではそれ単体あるいはスチレン樹脂を混合して、プラスチックモデル用の接着剤（通常塗布用と流し込み用）としての用途が広がっている。洗剤以外では汚れ落としやシールはがし用のスプレー等がある。また柑橘類系の芳香があるために香料としても利用されている。

説明ι-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.

天然物の起源It 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.

使用(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.

一般的な説明(S)-(-)-Limonene, a monoterpenoid compound, is mostly used in perfumery and in flavoring. On irradiation, it undergoes radiolysis, which leads to a reduction in the optical purity. (S)-(-)-Limonene also shows potent antimicrobial activity.

調製方法

製造方法d-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.

上流・下流製品情報

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上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

補足説明

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

関連反応

2 件
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関連ノート

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