p-멘타-6,8-다이엔-2-온, (R)-(-)

Carvone, (-)-

HCID 439570

기본 정보

CAS
6485-40-1
표준 SMILES
C=C(C)[C@@H]1CC=C(C)C(=O)C1
InChIKey
ULDHMXUKGWMISQ-SECBINFHSA-N
분자식
C10H14O
평균 분자량
150.22 g/mol
단동위원소 질량
150.10446507

개요

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

이름 및 식별자

우선 이름
Carvone, (-)-
IUPAC
(5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
현지명
p-멘타-6,8-다이엔-2-온, (R)-(-)
영어명
L(-)-Carvone
분자식
C10H14O
분자량
150.22

이름 및 동의어

(-)-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
이름 더 보기
ℓ-카르본p-멘타-6,8-다이엔-2-온,(R)-(-)p-멘타-6,8-다이엔-2-온, (R)-(-)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-

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
2.4
극성 표면적
17.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
1
무거운 원자 수
11

실험 및 물리화학적 성질

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 · 2건

Plant Growth Regulators

Active substance -> EU Pesticides database: Pending

LogP2.71

물리화학적 성질

녹는점
25 °C · 25°C
끓는 점
227 · 227-230 °C (lit.)
밀도
0.959 g/mL · 0.959 g/mL at 25 °C (lit.)
증기 밀도
5.2 · 5.2 (vs air)
증기압
0.4 mm · 0.4 mm Hg ( 20 °C)
굴절률
20 · n20/D 1.498

화학적 성질

clear colorless to pale yellow liquid

안전 및 규제

GHS 분류

GHS Classification · 6건

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)

유해성 정보

Regulatory Information · 5건

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 · 5건

Acute Tox. 4 (79.8%)

Skin sensitisation - category 1

Flammable liquids - Category 4

Skin sensitization - Category 1B

Skin Sens. 1

독성 정보

Toxicity Summary · 1건

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 · 1건

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.

안전 데이터

wgk
2
tsca
TSCA listed
rtecs
OS8650000
HS 번호
29142900
risk_code
22
hazard_code
Xn

화학 및 산업

약리 정보

Cellular LocationsExtracellular

용도 및 제조

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

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 · 2건

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 · 3건

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

응용 분야 · 3건

출처R-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.

용도(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.

일반 설명(-)-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.

공급사100 곳

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]

추가 설명

정의ChEBI: A carvone having (R) configuration.

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