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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 223
실험 및 물리화학적 성질
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
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
- FEMA
- 2249 · 2249 | CARVONE
- 인화점
- 192 °F · 192 °F
- 저장 조건
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- 용해도
- 클로로포름, 메탄올에 용해됨
- 물리적 상태
- 액체
- 색상
- 무색~담황색 투명
- 냄새
- 100 %에서 · 100.00%에서. 달콤한 스피어민트 허브민티
- 냄새 유형
- 민트 맛
- 생물학적 소스
- synthetic
- 수용성
- 실질적으로 불용성
- 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℃)
- 주요 응용
- 향료 및 향
- 화장품 원료 기능
- 향수향기향료
- 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℃
- NIST
- Carvone(6485-40-1)
- EPA
- 2 · 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5R)- (6485-40-1)
화학적 성질
clear colorless to pale yellow liquid
안전 및 규제
GHS 분류
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)
유해성 정보
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
독성 정보
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.
안전 데이터
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- OS8650000
- HS 번호
- 29142900
- risk_code
- 22
- hazard_code
- Xn
- safety_code
- 36-24/25
- F 고인화성물질
- 8-10-23
- Hazard Classifications
- Acute Tox. 4 OralSkin Sens. 1
- 스토리지 클래스
- 10 - Combustible liquids
화학 및 산업
약리 정보
용도 및 제조
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)]
응용 분야
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.
상·하류 제품 정보
상류 원료
하류 제품
공급사100 곳
추가 설명
정의ChEBI: A carvone having (R) configuration.
관련 반응
화합물 노트
불러오는 중…