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Merck

22070

(+)-Carvone

analytical standard

Synonym(s):

(+)-p-Mentha-6,8-diene 2-one, (S)-5-Isopropenyl-2-methyl-2-cyclohexenone

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About This Item

Empirical Formula (Hill Notation):
C10H14O
CAS Number:
Molecular Weight:
150.22
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
EC Number:
218-827-2
Beilstein/REAXYS Number:
2042970
MDL number:
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Product Name

(+)-Carvone, analytical standard

InChI key

ULDHMXUKGWMISQ-VIFPVBQESA-N

InChI

1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1

SMILES string

CC(=C)[C@H]1CC=C(C)C(=O)C1

grade

analytical standard

assay

≥98.5% (sum of enantiomers, GC)

optical activity

[α]20/D +61±2°, neat

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

refractive index

n20/D 1.499

bp

228-230 °C (lit.)

density

0.960 g/mL at 20 °C (lit.)

application(s)

agriculture
environmental
food and beverages

format

neat

Quality Level

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

General description

(+)-Carvone (S-carvone), is a monoterpene which has the ability to affect regulation of plant growth and development and microbial activity, it can also prevent sprouting in potato, through inhibition of the induction of phenylalanine ammonia-lyase (PAL) activity, thereby blocking suberisation.

Other Notes

This compound is commonly found in plants of the genus: carum mentha zingiber

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1A

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

204.1 °F - closed cup

flash_point_c

95.6 °C - closed cup

ppe

Eyeshields, Gloves


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Possible regulatory role of phenylalanine ammonia?lyase in the production of anthocyanins in asparagus (Asparagus officinalis L).
Flores, Francisco B., et al.
Journal of the Science of Food and Agriculture, 85.6, 925-930 (2005)
Mengyang Xuan et al.
Organic letters, 14(21), 5492-5495 (2012-10-26)
The total synthesis of the cAMP signaling pathway activator (-)-alotaketal A is reported. A convergent approach to the unusual alotane sesterterpenoid skeleton was employed, exploiting a remarkable LiDBB-mediated coupling of an (R)-carvone-derived δ-lactone with an allyl bromide side chain, followed
Peter Hewitson et al.
Journal of chromatography. A, 1218(36), 6072-6078 (2011-05-17)
Intermittent counter-current extraction (ICcE) has proved itself as a method for splitting compounds into streams and/or concentrating compounds in the column. In this paper a model mixture sample based on a modified GUESSmix (containing salicin, caffeine, aspirin, coumarin, salicylic acid
Philipp Klahn et al.
Organic letters, 14(5), 1250-1253 (2012-02-14)
The total synthesis of (+)-cyperolone, an eudesmane-derived sesquiterpenoid from Cyperus rotundus, is described. The de novo synthesis was accomplished via a 15 step sequence starting from (R)-(-)-carvone. The synthetic route features a platinum-catalyzed cycloisomerization to rapidly construct the bicyclic core
Elissavet E Anagnostaki et al.
Organic letters, 15(1), 152-155 (2012-12-22)
The synthesis of hydroxyelemane 5 from (R)-carvone and its utilization as a common synthetic scaffold to produce structurally diverse germacrane and guaiane sesquiterpenes are described. A highly enantio- and stereoselective biomimetic tandem oxy-Cope/ene rearrangement was used as the key reaction

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