Grundinformationen
- Standard-SMILES
C=C(C)[C@@H]1CC=C(C)C(=O)C1- InChIKey
ULDHMXUKGWMISQ-SECBINFHSA-N- Summenformel
- C10H14O
- Durchschnittliche Molmasse
- 150,22 g/mol
- Monoisotopische Masse
- 150,10446507
Überblick
(-)-carvone is a carvone having (R) configuration. It is an enantiomer of a (+)-carvone.
Namen und Bezeichner
- Bevorzugter Name
- Carvone, (-)-
- IUPAC
- (5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
- Lokaler Name
- (R)-(-)-Carvon
- Englischer Name
- L(-)-Carvone
- Summenformel
- C10H14O
- Molmasse
- 150.22
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
6485-40-1- PubChem CID
- 439570
- DTXSID
DTXSID7041413- ChEMBL
CHEMBL2229268- ChEBI
CHEBI:15400- UNII
- 5TO7X34D3D
- EC Number
- 229-352-5
- Nikkaji
- J15.688D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,4
- Polarare Oberfläche (TPSA)
- 17,1 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 11
- Formalladung
- 0
- Komplexität
- 223
Experimentelle und physikochemische Eigenschaften
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
Physikochemische Eigenschaften
- Schmelzpunkt
- 25 °C · 25°C
- Siedepunkt
- 227 · 227-230 °C (lit.)
- Dichte
- 0.959 g/mL · 0.959 g/mL at 25 °C (lit.)
- Dampfdichte
- 5.2 · 5.2 (vs air)
- Dampfdruck
- 0.4 mm · 0.4 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.498
- FEMA
- 2249 · 2249 | CARVONE
- Flammpunkt
- 192 °F · 192 °F
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- Löslichkeit
- Chloroform, Methanol
- Aggregatzustand
- Liquid
- Farbe
- Clear colorless to pale yellow
- Geruch (Odor)
- 100 % · at 100.00 %. sweet spearmint herbal minty
- Geruchsart
- minty
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- PRACTICALLY INSOLUBLE
- 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℃)
- Major Application
- flavors and fragrances
- Kosmetik-Inhaltsstoffe Funktionen
- PERFUMINGFRAGRANCEFLAVOURING
- 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 Datenbank
- 6485 · 6485-40-1(CAS DataBase Reference)
- NIST chemische Informationen
- Carvone(6485-40-1)
- EPA chemische Informationen
- 2 · 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5R)- (6485-40-1)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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)
Gefahrenhinweise
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
Toxikologische Informationen
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.
Sicherheitsdaten
- F
- 8-10-23
- wgk
- 2
- tsca
- TSCA listed
- hs_code
- 29142900
- RTECS-Nr.
- OS8650000
- risk_code
- 22
- hazard_code
- Xn
- safety_code
- 36-24/25
- Speicherklasse
- 10 - Combustible liquids
- Hazard Classifications
- Acute Tox. 4 OralSkin Sens. 1
Chemie und Industrie
Pharmakologische Informationen
Verwendung und Herstellung
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)]
Anwendungen
OccurrenceR-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.
Verwenden(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.
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Ergänzende Hinweise
DefinitionChEBI: A carvone having (R) configuration.
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