기본 정보
- CAS
5989-54-8- 표준 SMILES
C=C(C)[C@@H]1CC=C(C)CC1- InChIKey
XMGQYMWWDOXHJM-SNVBAGLBSA-N- 분자식
- C10H16
- 평균 분자량
- 136.23 g/mol
- 단동위원소 질량
- 136.12520051
개요
(4S)-limonene is an optically active form of limonene having (4S)-configuration. It is an enantiomer of a (4R)-limonene.
이름 및 식별자
- 우선 이름
- Limonene, (-)-
- IUPAC
- (4S)-1-methyl-4-prop-1-en-2-ylcyclohexene
- 현지명
- L-리모넨
- 영어명
- (S)-(-)-Limonene
- 분자식
- C10H16
- 분자량
- 136.23
이름 및 동의어
(-)-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
이름 더 보기
L-리모넨과산화물가가20mmol/L을초과하는ℓ-리모넨(S)-(-)-리모넨(-)-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
데이터베이스 식별자
- CAS
5989-54-8- PubChem CID
- 439250
- DTXSID
DTXSID6047078- ChEMBL
CHEMBL236688- ChEBI
CHEBI:15383- UNII
- 47MAJ1Y2NE
- EC Number
- 227-815-6
- Nikkaji
- J85.992C
물성
구조 계산 물성
- XLogP
- 3.4
- 극성 표면적
- 0 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 0
- 회전 가능 결합 수
- 1
- 무거운 원자 수
- 10
- 형식 전하
- 0
- 복잡도
- 163
실험 및 물리화학적 성질
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
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility0.0138 mg/mL at 25 °C
Flash Point48 °C
Melting Point-74.3 °C
Vapor Pressure1.44 [mmHg]
물리화학적 성질
- 녹는점
- -74 °C · -74°C
- 끓는 점
- 175 · 175-177 °C(lit.)
- 밀도
- 0.844 g/mL · 0.844 g/mL at 25 °C(lit.)
- 증기 밀도
- 4.7 · 4.7 (vs air)
- 증기압
- 3 mm · <3 mm Hg ( 14.4 °C)
- 굴절률
- 20 · n20/D 1.471(lit.)
- 인화점
- 119 °F · 119 °F
- 저장 조건
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- 용해도
- 클로로포름(적게), 에탄올(약간), 메탄올(약간)에 용해됨
- 물리적 상태
- 액체
- 색상
- 무색~담황색 투명
- 냄새
- 100 %에서 · 100.00%에서. 테르펜 파인 허브 페퍼리
- 냄새 유형
- 테르펜
- 생물학적 소스
- synthetic
- 폭발한계
- 0.7 · 0.7-6.1%(V)
- 수용성
- 불용성
- Merck
- 14 · 14,5493
- BRN
- 2323991 · 2323991
- Henry's Law Constant
- 3.7 · 3.7×10-4 mol/(m3Pa) at 25℃, Schuhfried et al. (2015)
- 안정성
- 안정적인. 강한 산화제와 호환되지 않습니다. 가연성.
- 주요 응용
- 향료 및 향
- InChI
- 1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m1/s1
- InChIKey
- XMGQYMWWDOXHJM-SNVBAGLBSA-N
- SMILES
- CC(=C)[C@H]1CCC(C)=CC1
- LogP
- 4.38 at · 4.38 at 37℃
- NIST
- 1 · Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-(5989-54-8)
- EPA
- 1 · Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)- (5989-54-8)
화학적 성질
colourless liquid with lemon odour
안전 및 규제
GHS 분류
GHS Classification
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)
유해성 정보
Regulatory Information
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
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
Flam. Liq. 3 (100%)
Flammable liquid - category 3
Flam. Liq. 3
독성 정보
Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
안전 데이터
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- OS8350000
- ridadr
- UN 2052 3/PG 3
- HS 번호
- 29029090
- risk_code
- 10-38-43-50/53
- hazard_code
- Xi,N
- safety_code
- 24-37-60-61
- 포장분류
- III
- 위험 등급
- 3
- F 고인화성물질
- 8-10-23
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Flam. Liq. 3Skin Irrit. 2Skin Sens. 1B
- 스토리지 클래스
- 3 - Flammable liquids
화학 및 산업
약리 정보
Metabolism/Metabolites(-)-limonene has known human metabolites that include Carveol and Perillyl alcohol.
Cellular LocationsExtracellular
용도 및 제조
Uses
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
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
응용 분야
개요ι-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.
출처It 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.
용도(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.
일반 설명(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.
제조 방법
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.
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추가 설명
정의ChEBI: An optically active form of limonene having (4S)-configuration.
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