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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 223
実験および物理化学的性質
Pesticides
Plant Growth Regulators
Active substance -> EU Pesticides database: Pending
Solubility
1.31 mg/mL at 25 °C
soluble in propylene glycol and most fixed oils; insoluble in glycerol; miscible with alcohol
1 ml in 2 ml 70% alcohol (in ethanol)
Boiling Point
227.00 to 230.00 °C. @ 760.00 mm Hg
231 °C
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)
- 屈折率
- 20 · n20/D 1.498
- FEMA
- 2249 · 2249 | CARVONE
- 闪点
- 192 °F · 192 °F
- 貯蔵温度
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- 溶解性
- クロロホルム、メタノール
- 外見
- 液体
- 色
- 無色透明~淡黄色
- 臭い (Odor)
- 100 %で。スイートスペアミントハーブミント · 100.00%で。スイートスペアミントハーブミント
- においのタイプ
- ミント系
- 由来生物
- synthetic
- 水溶解度
- 実質的に不溶
- Merck
- 14 · 14,1874
- JECFA Number
- 380 · 380
- BRN
- 2206714 · 2206714
- Henry's Law Constant
- 4.9 · 4.9×10-1 mol/(m3Pa) at 25℃, Amoore and Buttery (1978)
- Dielectric constant
- 11 · 11.0(22℃)
- 主な用途
- フレーバーそして香料
- 化粧品成分の機能
- 香料香料香料
- InChI
- 1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1
- InChIKey
- ULDHMXUKGWMISQ-SECBINFHSA-N
- SMILES
- CC(=C)[C@@H]1CC=C(C)C(=O)C1
- LogP
- 2.74 at · 2.74 at 20-37℃
- CAS データベース
- 6485 · 6485-40-1(CAS DataBase Reference)
- NISTの化学物質情報
- Carvone(6485-40-1)
- EPAの化学物質情報
- 2 · 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5R)- (6485-40-1)
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
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
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
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
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
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
- 化審法
- (3)-2402
- 消防法
- 危-4-3-III
- hazard_code
- Xn
- safety_code
- 36-24/25
- Hazard Classifications
- Acute Tox. 4 OralSkin Sens. 1
- ストレージクラス
- 10 - Combustible liquids
化学と産業
薬理情報
用途と製造
IFRA Fragrance Standards
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
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
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information
Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing
2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5R)-: ACTIVE
Restriction Limits in the Finished Product (%)
0.2 [Products applied to the lips]
0.06 [Products applied to the axillae]
0.02 [Products applied to the face/body using fingertips]
0.59 [Products related to fine fragrances]
0.2 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]
0.039 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]
応用分野
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.
上流・下流製品情報
上流原料
下流製品
サプライヤー100 社
補足説明
定義ChEBI: A carvone having (R) configuration.
関連反応
化合物ノート
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