(R)-(-)-カルボン

Carvone, (-)-

HCID 439570

基本情報

CAS
6485-40-1
標準SMILES
C=C(C)[C@@H]1CC=C(C)C(=O)C1
InChIKey
ULDHMXUKGWMISQ-SECBINFHSA-N
分子式
C10H14O
平均分子量
150.22 g/mol
単同位体質量
150.10446507

概要

(-)-carvone is a carvone having (R) configuration. It is an enantiomer of a (+)-carvone.

名称と識別子

優先名称
Carvone, (-)-
IUPAC
(5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
現地名
(R)-(-)-カルボン
英語名
L(-)-Carvone
分子式
C10H14O
分子量
150.22

名称と別名

(-)-Carvone6485-40-1l-Carvone(R)-(-)-CarvoneL(-)-Carvone(R)-CarvoneLevo-carvoneCarvone, (-)-(4R)-Carvone(5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one(-)-p-Mentha-6,8-dien-2-one(-)-(R)-Carvone
名称をさらに表示
(R)-(-)-カルボン2-メチル-5β-(1-メチルエテニル)-2-シクロヘキセン-1-オン(R)-p-メンタ-6(1),8-ジエン-2-オン(R)-5β-イソプロペニル-2-メチル-2-シクロヘキセン-1-オン(4R)-p-メンタ-1,8-ジエン-6-オン[R,(-)]-2-メチル-5-(1-メチルビニル)-2-シクロヘキセン-1-オン(4R)-p-メンタ-1(6),8-ジエン-2-オン(5R)-2-メチル-5-イソプロペニル-2-シクロヘキセン-1-オン(5R)-2-メチル-5α-イソプロペニルシクロヘキセン-3-オン(5R)-2-メチル-5-イソプロペニル-1-シクロヘキセン-3-オン2-メチル-5β-イソプロペニル-2-シクロヘキセン-1-オン(5R)-2-メチル-5β-イソプロペニル-2-シクロヘキセン-1-オン[R,(-)]-カルボンL-(-)-カルボン(R)-5-イソプロペニル-2-メチル-2-シクロヘキセン-1-オン[R,(-)]-6(1),8-p-メンタジエン-2-オン(R)-2-メチル-5-(1-メチルエテニル)-2-シクロヘキセン-1-オン5β-イソプロペニル-2-メチル-2-シクロヘキセン-1-オン(5R)-5-イソプロペニル-2-メチル-2-シクロヘキセン-1-オンl-カルボンCARVOLFEMA 2249(?)-Carvone(R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)-l-p-mentha-1(6),8-dien-2-one
l-Carvone (natural)UNII-5TO7X34D3D5TO7X34D3DCHEBI:15400l-6,8(9)-p-Menthadien-2-onel-1-Methyl-4-isopropenyl-6-cyclohexen-2-one(-)-(4R)-carvoneCARVONE, L-

データベース識別子

CAS
6485-40-1
PubChem CID
439570
DTXSID
DTXSID7041413
ChEMBL
CHEMBL2229268
ChEBI
CHEBI:15400
UNII
5TO7X34D3D
EC Number
229-352-5
Nikkaji
J15.688D

物性

構造計算による物性

XLogP
2.4
極性表面積
17.1 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
1
重原子数
11

実験および物理化学的性質

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
CosmeticsCosmetics ingredient -> Flavor; Fragrance; Other (Specify)
SpringerMaterials PropertiesOptical coefficient
FragrancesFragrance Ingredient (L-Carvone) -> IFRA transparency List
Pesticides · 2 件

Plant Growth Regulators

Active substance -> EU Pesticides database: Pending

LogP2.71

物理化学的性質

融点
25 °C · 25°C
比旋光度
-57 · -57 º (neat)
沸点
227 · 227-230 °C (lit.)
比重(密度)
0.959 g/mL · 0.959 g/mL at 25 °C (lit.)
蒸気密度
5.2 · 5.2 (vs air)
蒸気圧
0.4 mm · 0.4 mm Hg ( 20 °C)

化学的性質

化学的特性clear colorless to pale yellow liquid

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

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

Warning

H302 (79.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 5 件

Chemical: 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)-

Regulation (EC) No 1831/2003 (amended)

2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5R)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (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)

REACH registered substance: L-p-mentha-1(6),8-dien-2-one (EC: 229-352-5)

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

Hazard Classes and Categories · 5 件

Acute Tox. 4 (79.8%)

Skin sensitisation - category 1

Flammable liquids - Category 4

Skin sensitization - Category 1B

Skin Sens. 1

毒性情報

Toxicity Summary · 1 件

The existing information was reviewed by the independent Expert Panel for Fragrance Safety and supports the use of l-Carvone as described in this safety assessment. Data show that it is not genotoxic and provided a No Expected Sensitization Induction Level (NESIL) of 2600 μg/cm2 for the skin sensitization endpoint. Data provided a calculated Margin of Exposure (MOE) greater than 100 for the repeated dose toxicity and reproductive toxicity endpoints. l-carvone is not phototoxic/photoallergenic based on an evaluation the data and the ultraviolet/visible (UV/Vis) spectra. The local respiratory toxicity endpoint was evaluated using the Threshold of Toxicological Concern (TTC) for a Cramer Class II material (0.47 mg/day); the exposure to l-carvone is below the TTC.

Environmental Fate/Exposure Summary · 1 件

The existing information was reviewed by the independent Expert Panel for Fragrance Safety and supports the use of l-carvone as described in this safety assessment. It was found not to be persistent, bioaccumulative, and toxic (PBT) as per the International Fragrance Association (IFRA) Environmental Standards, and its risk quotients, based on its current volume of use in Europe and North America (i.e., Predicted Environmental Concentration/Predicted No Effect Concentration [PEC/PNEC]), are less than 1.

安全データ

F
8-10-23
wgk
2
tsca
TSCA listed
rtecs
OS8650000
hs_code
29142900
risk_code
22

化学と産業

薬理情報

Cellular LocationsExtracellular

用途と製造

U.S. Production2023: 100,000 - <250,000 lb
Consumer UsesFragrance
Industry UsesFragrance
IFRA Fragrance Standards · 6 件

Carvone

99-49-0 (Carvone):; p-Mentha-6,8-dien-2-one; 1-Methyl-4-isopropenyl-6-cyclohexen-2-one; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-; 5-Isopropenyl-2-methylcyclohex-2-en-1-one; 6,8(9)-p-Menthadien-2-one.; 2244-16-8 (d-Carvone):; (S)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-one; d-p-Mentha-6,8(9)-dien-2-one; d-1-Methyl-4-isopropenyl-6-cyclohexen-2-one; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (S)-.; 6485-40-1 (l-Carvone):; l-p-Mentha-1(6),8-dien-2-one; l-p-Mentha-6,8(9)-dien-2-one; l-1-Methyl-4-isopropenyl-6-cyclohexen-2-one; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)-; 5-Isopropenyl-2-methylcyclohex-2-en-1-one.

IFRA_STD_016.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

Household Products · 2 件

Cosmetics product ingredient: 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one; (5R)-2-Methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one;(5S)-2-Methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one (Carvone)

Information on 30 consumer products that contain L-Carvone in the following categories is provided:

Use Classification · 3 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

応用分野 · 4 件

用途香料、香味料、口腔衛生製品におけるミント香料

天然物の起源R-Carvone is the main substance in spearmint oil, also present in toothpastes; it is the cause of delayed-type allergy resulting in cheilitis, but Hansson et al. also described a case of angioedema of the lips appearing within minutes after contact with toothpaste, with an open test resulting in an immediate and strong reaction to carvone.

使用(R)-(-)-Carvone is used in the flavor and food industry such as chewing gum additives. It is used in air freshening products such as in essential oils as well as in aromatherapy and alternative medicine. It is used to prepare carvomenthol, carvomenthone, dihydrocarvone, carveol and limonene. It reacts with lithium dimethylcuprate to place a methyl group trans to the isopropenyl group with good stereoselectivity. It is also used as a mosquito repellent and prevent premature sprouting of potatoes. Further, it is employed as an important starting material for the synthesis of enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1 and (4S,6R,7R)-trihydroxy-1-octyne derivatives. It is utilized as a vital raw material for the asymmetric total synthesis of natural products. In addition to this, it is used as a chiral starting material.

一般的な説明(-)-Carvone, a monoterpene ketone which is the main active component of mentha plant species like Mentha spicata. It has antinociceptive activity which is found to be associated with decreased peripheral nerve excitability.

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補足説明

定義ChEBI: A carvone having (R) configuration.

関連反応

5 件

化合物ノート

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