Methyl-3-oxo-2-pentylcyclopentanacetat

Bezeichnung:Methyl-3-oxo-2-pentylcyclopentanacetat

CAS-Nr24851-98-7

Englisch Name:Methyl dihydrojasmonate

CBNumberCB9377525

SummenformelC13H22O3

Molgewicht226.31

MOL-Datei24851-98-7.mol

Synonyma

Methyl-3-oxo-2-pentylcyclopentanacetat

Methyl-3-oxo-2-pentylcyclopentanacetat physikalisch-chemischer Eigenschaften

Siedepunkt	110 °C/0.2 mmHg (lit.)
Dichte	0.998 g/mL at 25 °C (lit.)
Dampfdruck	0.21Pa at 25℃
Brechungsindex	n20/D 1.459(lit.)
FEMA	3408 \| METHYL DIHYDROJASMONATE
Flammpunkt	>230 °F
storage temp.	2-8°C
Löslichkeit	H₂O: insoluble
Aggregatzustand	Oil
Farbe	Clear Colorless
Geruch (Odor)	at 100.00 %. floral oily jasmin green lactonic tropical natural
Geruchsart	floral
Wasserlöslichkeit	399.8mg/L(25 ºC)
JECFA Number	1898
Merck	14,6052
InChIKey	KVWWIYGFBYDJQC-GHMZBOCLSA-N
LogP	2.93 at 22℃
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	Methyl 3-oxo-2-pentyl-cyclopentaneacetate (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.)

Gefahreninformationscode (GHS)

Methyl dihydrojasmonate 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
Verwenden
Methyl (3-Oxo-2-pentylcyclopentyl)acetate is used in the preparation of hydrogels as delivery systems for the slow release of bioactive carbonyl derivatives.
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.
Allgemeine Beschreibung
Methyl dihydrojasmonate is a fragrance ingredient mainly used in the perfumes, fragrance formulations, personal care and cosmetic products. It occurs naturally in pine honey and rhododendron honey.
Flammability and Explosibility
Non flammable
Handelsname
Claigeon®, Cepionate®(Nippon Zeon),Hedione®,Hedione®HC (Firmenich), Kharismal® (IFF).

Methyl dihydrojasmonate Upstream-Materialien And Downstream Produkte

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

24851-98-7, Methyl dihydrojasmonate Verwandte Suche:

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