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Methyl-3-oxo-2-pentylcyclopentanacetat Produkt Beschreibung

Methyl dihydrojasmonate Struktur
24851-98-7
CAS-Nr.
24851-98-7
Bezeichnung:
Methyl-3-oxo-2-pentylcyclopentanacetat
Englisch Name:
Methyl dihydrojasmonate
Synonyma:
HEDION;hedione;FEMA 3408;MDJ SUPER;kharismal;CAIGEON 98%;Fema no. 3408;CEPIONATE 95%;Einecs 246-495-9;Methyldihydrojasonate
CBNumber:
CB9377525
Summenformel:
C13H22O3
Molgewicht:
226.31
MOL-Datei:
24851-98-7.mol

Methyl-3-oxo-2-pentylcyclopentanacetat Eigenschaften

Siedepunkt:
110 °C0.2 mm Hg(lit.)
Dichte
0.998 g/mL at 25 °C(lit.)
Brechungsindex
n20/D 1.459(lit.)
FEMA 
3408 | METHYL DIHYDROJASMONATE
Flammpunkt:
>230 °F
Löslichkeit
H2O: insoluble
Merck 
14,6052
JECFA Number
1898
InChIKey
KVWWIYGFBYDJQC-GHMZBOCLSA-N
CAS Datenbank
24851-98-7(CAS DataBase Reference)
NIST chemische Informationen
Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester(24851-98-7)
EPA chemische Informationen
Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester(24851-98-7)

Sicherheit

S-Sätze: 23-24/25
WGK Germany  2
RTECS-Nr. GY2453800
HS Code  29183000
Toxizität LD50 (g/kg): >5 orally in rats; >5 dermally in rabbits (Food Chem. Toxicol.)

Methyl-3-oxo-2-pentylcyclopentanacetat Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:

S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
S24/25:Berührung mit den Augen und der Haut vermeiden.

Beschreibung

Methyl dihydrojasmonate has a powerful sweet-floral, jasminelike, somewhat fruity odor. This is the odoriferous component in jasmine oil (Jasminum gradiflorum L.). May be prepared by condensation of 2-pentyl-2-cyclopenten-l-one with ethyl malonate, followed by hydrolysis, decarboxylation, and methylation.

Chemische Eigenschaften

Methyl dihydrojasmonate has a powerful sweet-floral, jasmine-like, somewhat fruity odor. This compound is the odoriferous component of jasmine oil (Jasminum gradiflorum L.)

Chemische Eigenschaften

Methyl dihydrojasmonate is a jasmine fragrance that is closely related to methyl jasmonate, which occurs in jasmine oil. Methyl dihydrojasmonate has been identified in tea. It is a liquid with a typical fruity, jasmine-like blossom odor.
Methyl dihydrojasmonate is prepared by Michael addition of malonic acid esters to 2-pentyl-2-cyclopenten-l-one, followed by hydrolysis and decarboxylation of the resulting (2-pentyl-3-oxocyclopentyl)malonate, and esterification of the (2-pentyl-3-oxocyclopentyl)acetic acid [304]. 2-Pentyl-2-cyclopenten-1-one is prepared by an aldol condensation between cyclopentanone and valeraldehyde and subsequent isomerization of the resulting 2- pentylidenecyclopentanone or by palladium catalyzed decarboxylation of allyl 2-oxo-1-pentylcyclopentanecarboxylates.
Dealkoxycarbonylation of the malonate can also be accomplished directly with water at elevated temperature.
Methyl dihydrojasmonate of the aforementioned quality consists of a 9 : 1 equilibrium mixture of the trans- and cis-isomers. However, methyl cisdihydrojasmonate is the much more intensive isomer, with a threshold about 20 times lower than that of the trans-isomer. Therefore, methyl dihydrojasmonate qualities with enriched portions of the cis-isomer are also marketed.
These “high-cis” products are colorless liquids with extremely powerful jasmine character.Thedifferent commercial qualities may contain different amounts of the cis-isomer.
High-cis methyl dihydrojasmonate is a valuable material in fine fragrances but suffers from stability problems due to its tendency to isomerize into the equilibrium mixture and, therefore, has only limited usage in other perfumery applications.
High-cis methyl dihydrojasmonate can be produced from the equilibrium mixture by special distillation techniques in which isomerization is effected by the action of sodium carbonate. A high proportion of cis methyl dihydrojasmonate can also be obtained by hydrogenation of methyl dehydrodihydrojasmonate, which is accessible from 1(2-furyl)-hexanol via rearrangement, isomerization, etherification, and condensation with dimethyl malonate.
For other stereoselective synthetic approaches, see review.
Of all possible isomers, the (+)-(1R)-cis-isomer possesses the most characteristic and intensive jasmine odor.Therefore, an industrially feasible process for the production of a methyl dihydrojasmonate with a high portion of this isomer has been developed. The process comprises the catalytic hydrogenation of the corresponding cyclopenteneacetic acid in the presence of a ruthenium(II) complexwith chiral ligands and subsequent esterification.
Methyl dihydrojasmonate is used in perfumery for blossom fragrances, particularly in jasmine types.

Occurrence

Reported found in jasmine oil (Jasminum gradiflorum L.) and black tea

synthetische

By condensation of 2-pentyl-2-cyclopenten-1-one with ethyl malonate, followed by hydrolysis, decarboxylation and methylation

Taste threshold values

Taste characteristics at 20 ppm: sweet, floral, citrus, fruity and berry with tutti-frutti undernotes.

Handelsname

Claigeon®, Cepionate®(Nippon Zeon),Hedione®,Hedione®HC (Firmenich), Kharismal® (IFF).

Methyl-3-oxo-2-pentylcyclopentanacetat Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Methyl-3-oxo-2-pentylcyclopentanacetat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 151)Lieferanten
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Mainchem Co., Ltd.
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24851-98-7(Methyl-3-oxo-2-pentylcyclopentanacetat)Verwandte Suche:


  • 3-oxo-2-pentyl-cyclopentaneaceticacimethylester
  • Cyclopentaneaceticacid,3-oxo-2-pentyl-,methylester
  • hedione
  • CEPIONATE A.K.A. METHYL EPI-DIHYDROJASMONATE
  • (3-Oxo-2-pentyl-cyclopentyl)-acetic acid methyl ester
  • Methyl Dihydrojasmonate (cis- and trans- mixture)
  • METHYL DIHYDROJASMONATE HC
  • (2-Pentyl-3-oxocyclopentyl)acetic acid methyl ester
  • 2-Amyl-3-oxo-1-cyclopentaneacetic acid methyl ester
  • Dihydrojasmonic acid methyl
  • Methyl epi-dihydrojasmonate
  • methyl3-oxo-2-pentylcyclopentaneacetate
  • 2-AMYLCYCLOPENTAN-1-ONE-3-ACETIC ACID METHYL ESTER
  • METHYL-(2-PENTYL-3-OXOCYCLOPENTAN-1-YL) ACETATE
  • METHYL 3-OXO-2-PENTYL-1-CYCLOPENTANEACETATE
  • METHYL (3-OXO-2-PENTYLCYCLOPENTYL)ACETATE
  • METHYL DIHYDROJASMONATE
  • METHYLDIHYDRO JASMONATE (CIS)
  • DIHYDROJASMONIC ACID METHYL ESTER
  • FEMA 3408
  • Methyl epi-dihydrojysmonate
  • 3-(METHYLTHIO)-1-PROPANOL 98+%
  • 3-Oxo-2-pentylcyclopentaneaceticacidmethylester
  • Claigeon(R),Cepionate(R)orSuperCepionate(R)
  • Methyldihydrojasonate
  • hedione(r) (firmenich)
  • HEDION
  • Methyl-3-oxo-2-pentylcyclopentanacetat
  • MDJ SUPER
  • CAIGEON 98%
  • CAIGEON A.K.A. CYCLOPENTANEACETIC ACID, 3-OXO-2-
  • CEPIONATE 95%
  • Nano Liposomal sodium tetrahydrojasmonate
  • Methyl dihydrojasmonate(EDC)
  • (±)-9,10-DIHYDROJASMONIC ACID METHYL ESTER (MeDJA)
  • Einecs 246-495-9
  • Fema no. 3408
  • Methyl DihydrojasMonate 
  • Methyl dihydrojasMonate(MDJ)
  • 2-Amylcyclopentan-1-one-3-acetic Acid Methyl Ester Dihydrojasmonic Acid Methyl Ester Methyl 3-Oxo-2-pentyl-1-cyclopentaneacetate
  • Methyl dihydrojasMonate (cis-and trans-Mixture)
  • Methyl dihydrojasmonate Methyl (3-oxo-2-pentylcyclopentyl)acetate
  • Methyl dihydrojasmonate, mixture of cis and trans
  • kharismal
  • methyl(2-pentyl-3-oxocyclopentyl)acetate
  • methyl dihydrojasmonate/Hedione
  • 24851-98-7
  • Alphabetical Listings
  • Flavors and Fragrances
  • M-N
  • -
  • As an aroma chemical for use in flavor, fragrance, and other applications
  • Inhibitors
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