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Carvone information


Carvone
Carvone
Names
Preferred IUPAC name
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Other names
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enone
2-Methyl-5-(1-methylethenyl)-2-cyclohexenone[1]
Δ6:8(9)-p-Menthadien-2-one
1-Methyl-4-isopropenyl-Δ6-cyclohexen-2-one
Carvol (obsolete)
Identifiers
CAS Number
  • 99-49-0 (R/S) checkY
  • 6485-40-1 (R) checkY
  • 2244-16-8 (S) checkY
3D model (JSmol)
  • (R): Interactive image
  • (S): Interactive image
ChEBI
  • CHEBI:38265 checkY
ChEMBL
  • ChEMBL15676 checkY
ChemSpider
  • 21106424 (R/S) checkY
  • 15855 (S) checkY
  • 388655 (R) checkY
ECHA InfoCard 100.002.508 Edit this at Wikidata
KEGG
  • C01767 checkY
PubChem CID
  • 7439
RTECS number
  • OS8650000 (R)
    OS8670000 (S)
UNII
  • 75GK9XIA8I (R/S) checkY
  • 5TO7X34D3D (R) checkY
  • 4RWC1CMS3X (S) checkY
CompTox Dashboard (EPA)
  • DTXSID8047426 Edit this at Wikidata
InChI
  • InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3 checkY
    Key: ULDHMXUKGWMISQ-UHFFFAOYSA-N checkY
  • InChI=1/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3
    Key: ULDHMXUKGWMISQ-UHFFFAOYAB
SMILES
  • (R): O=C1C[C@@H](C\C=C1\C)C(C)=C
  • (S): O=C1C[C@H](C\C=C1\C)C(C)=C
Properties
Chemical formula
C10H14O
Molar mass 150.22 g/mol
Appearance Clear, colorless liquid
Density 0.96 g/cm3
Melting point 25.2 °C (77.4 °F; 298.3 K)
Boiling point 231 °C (448 °F; 504 K) (91 °C @ 5 mmHg)
Solubility in water
Insoluble (cold)
Slightly soluble (hot)/soluble in trace amounts
Solubility in ethanol Soluble
Solubility in diethyl ether Soluble
Solubility in chloroform Soluble
Chiral rotation ([α]D)
−61° (R)-Carvone
61° (S)-Carvone
Magnetic susceptibility (χ)
−92.2×10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
GHS labelling:
Pictograms
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word
Danger
Hazard statements
H304, H315, H317, H411
Precautionary statements
P261, P264, P270, P272, P273, P280, P301+P310, P301+P312, P302+P352, P321, P330, P331, P332+P313, P333+P313, P362, P363, P391, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Safety data sheet (SDS) External MSDS
Related compounds
Related ketone
menthone
dihydrocarvone
carvomenthone
Related compounds
limonene, menthol,
p-cymene, carveol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Carvone is a member of a family of chemicals called terpenoids.[2] Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway (Carum carvi), spearmint (Mentha spicata), and dill.[3]

  1. ^ Vollhardt, K. Peter C.; Schore, Neil E. (2007). Organic Chemistry (5th ed.). New York: W. H. Freeman. p. 173.
  2. ^ Simonsen, J. L. (1953). The Terpenes. Vol. 1 (2nd ed.). Cambridge: Cambridge University Press. pp. 394–408.
  3. ^ De Carvalho, C. C. C. R.; Da Fonseca, M. M. R. (2006). "Carvone: Why and how should one bother to produce this terpene". Food Chemistry. 95 (3): 413–422. doi:10.1016/j.foodchem.2005.01.003.

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Carvone

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Carvone is a member of a family of chemicals called terpenoids. Carvone is found naturally in many essential oils, but is most abundant in the oils from...

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Limonene

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manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. The less common...

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Chirality

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biological actions. For example,(+)-Carvone is responsible for the smell of caraway seed oil, whereas (–)-carvone is responsible for smell of spearmint...

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Caraway

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When ground, caraway seeds yield up to 7.5% of volatile oil, mostly D-carvone, and 15% fixed oil of which the major fatty acids are oleic, linoleic,...

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Carvone reductase

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Carvone reductase (EC 1.3.99.25) is an enzyme with systematic name (+)-dihydrocarvone:acceptor 1,6-oxidoreductase. This enzyme catalyses the following...

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Thyme

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ground cover, and has a very strong caraway scent due to the chemical carvone. Thymus praecox (mother of thyme, wild thyme), is cultivated as an ornamental...

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Spearmint

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oil of spearmint. The most abundant compound in spearmint oil is R-(–)-carvone, which gives spearmint its distinctive smell. Spearmint oil also contains...

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Angelica archangelica

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camphene, myrcene, β-phellandrene, limonene, caryophyllene, borneol, carvone and others. Both the seeds and roots contain coumarins and furocoumarins...

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Minthostachys mollis

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(−)-β-pinene (−)-α-pinene limonene isomenthone piperic acid eucalyptol carvone In the flowering tops 19 compounds were identified in the essential oil...

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Monoterpene

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Menthol is a monocyclic monoterpenoid Limonene is a monocyclic monoterpene Carvone is a monoterpenoid Hinokitiol is a monoterpenoid, a tropolone derivative...

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Dill

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named Anethus who was transformed into the plant. Apiole and dillapiole Carvone Limonene Myristicin Umbelliferone Fresh and dried dill leaves (sometimes...

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Kumquat

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isopropyl propanoate (1.8%) and terpinyl acetate (1.26%); ketones such as carvone (0.175%); and a range of aldehydes such as citronellal (0.6%) and 2-methylundecanal...

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Propenyl

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synthesizable from ketene. Several terpenes feature 2-propenyl substituents: carvone limonene Propene Functional group Linstrumelle, Gerard; Krieger, Jeanne...

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Aluminium chloride

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reaction, such as the addition of 3-buten-2-one (methyl vinyl ketone) to carvone: It is used to induce a variety of hydrocarbon couplings and rearrangements...

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Terpene

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acid-induced carbocation formation. Selected terpenes Limonene, a monoterpene. Carvone is a monoterpenoid, a modified monoterpene. Pinene, a monoterpene which...

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C10H14O

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g/mol, exact mass: 150.104465 u) can refer to: o-sec-Butylphenol Carvacrol Carvone Chrysanthenone Cumyl alcohol 2-Ethyl-4,5-dimethylphenol, a phenolic compound...

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Carvacrol

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heating of camphor and iodine or carvone with glacial phosphoric acid have also been demonstrated. The dehydrogenation of carvone with a palladium-carbon catalyst...

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Hyuganatsu

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fruit's oil is higher than other citrus fruits in trans-β-farnesene, l-carvone, and has a higher number of ketones. Amanatsu Japanese citrus Ōgonkan Willard...

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Terpenoid

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prenol Monoterpenoids Monoterpenes 2 10 C10H16 Bornyl acetate, camphor, carvone, citral, citronellal, citronellol, geraniol, eucalyptol, hinokitiol, iridoids...

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Mentha

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compound primarily responsible for the aroma and flavor of spearmint is L-carvone. Mints are used as food plants by the larvae of some Lepidoptera species...

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Aroma compound

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substance, like propane, natural gas, or hydrogen, as a safety measure. Note: Carvone, depending on its chirality, offers two different smells. Furaneol (strawberry)...

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Menthol

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skin rash, tremor, vomiting, and vertigo. Medicine portal Aroma compound Carvone Chlorobutanol Ethyl benzoate Ethyl salicylate Menthoxypropanediol Methyl...

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Carvonic acid

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by metabolism of carvone in humans. Engel, W. (2001). "In Vivo Studies on the Metabolism of the Monoterpenes S-(+)- and R-(−)-Carvone in Humans Using the...

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Canarium luzonicum

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constituents include phellandrene, limonene, elemol, elemicin, terpineol, carvone, and terpinolene. The seed kernels are used for food, both raw and cooked...

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Strange Days at Blake Holsey High

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affects several test tubes and Principal Durst, in trying to transform carvone to its left-handed form, exchanges personalities with Professor Z. At the...

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