24851-98-7 Usage
Description
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.
Chemical Properties
Different sources of media describe the Chemical Properties of 24851-98-7 differently. You can refer to the following data:
1. Methyl dihydrojasmonate has a powerful sweet-floral, jasmine-like, somewhat fruity odor. This compound is the odoriferous component of jasmine oil (Jasminum gradiflorum L.)
2. 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
Uses
Methyl (3-Oxo-2-pentylcyclopentyl)acetate is used in the preparation of hydrogels as delivery systems for the slow release of bioactive carbonyl derivatives.
Preparation
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.
General Description
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
Nonflammable
Trade name
Claigeon?, Cepionate?(Nippon Zeon),Hedione?,Hedione?HC
(Firmenich), Kharismal? (IFF).
Check Digit Verification of cas no
The CAS Registry Mumber 24851-98-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,8,5 and 1 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 24851-98:
(7*2)+(6*4)+(5*8)+(4*5)+(3*1)+(2*9)+(1*8)=127
127 % 10 = 7
So 24851-98-7 is a valid CAS Registry Number.
InChI:InChI=1/C13H22O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h10-11H,3-9H2,1-2H3
24851-98-7Relevant articles and documents
Preparation method of 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate
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Paragraph 0063; 0067-0069; 0073-0075; 0079-0081; 0085-0087;, (2020/09/20)
The invention relates to a preparation method of 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate. The preparation method of the 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate comprises the following step: in the presence of a transition metal complex and a catalytic additive, reacting 2-pentyl-2-cyclopentenone with dimethyl malonate in a reaction solvent to obtain the 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate. According to the preparation method provided by the invention, a sodium methoxide strong base catalyst is not needed, the generation of salt-containing wastewater is avoided, the method is environment-friendly and high in yield, and meanwhile, the recycling of the catalyst is realized.
Method of manufacturing methylcyclopentanone deriv. (by machine translation)
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, (2018/11/22)
PROBLEM TO BE SOLVED: To provide an efficient method for producing a cyclopentanone derivative usable as an intermediate for a methyl (3-oxocyclopentyl)acetate derivative useful as a perfumery material.SOLUTION: The method for producing the cyclopentanone derivative expressed by general formula (III) comprises Michael addition reaction of a 2-cyclopenten-1-one derivative and an ester compound in the presence of a solid base catalyst containing a phosphazene base or a guanidine base. In the formula, Ris a 1-10C hydrocarbon group; Ris 1-4C alkyl; and Ris 1-4C alkyl or alkoxyl.
METHOD FOR PRODUCING OF 2-ALKYL-2-CYCLOALKEN-1-ONE
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, (2011/02/26)
The present invention relates to [1] a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), which includes the step of subjecting a 2-(1-hydroxyalkyl)cycloalkan-1-one to dehydration and isomerization in the co-existence of an acid and a platinum group metal catalyst, and [2] a process for producing an alkyl(3-oxo-alkylcycloalkyl)acetate which is useful as a perfume material, using the 2-alkyl-2-cycloalken-1-one: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.
