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Methyl dihydrojasmonate

Product Name
Methyl dihydrojasmonate
CAS No.
24851-98-7
Chemical Name
Methyl dihydrojasmonate
Synonyms
hedione;MDJ;HEDION;kharismal;Einecs 246-495-9;Methyl epi-dihydrojasmonate;DIHYDROJASMONIC ACID METHYL ESTER;Methyl-3-oxo-2-pentylcyclopentanacetat;methyl(2-pentyl-3-oxocyclopentyl)acetate;3-oxo-2-pentyl-cyclopentaneaceticacimethylester
CBNumber
CB9377525
Molecular Formula
C13H22O3
Formula Weight
226.31
MOL File
24851-98-7.mol
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Methyl dihydrojasmonate Property

Boiling point:
110 °C/0.2 mmHg (lit.)
Density 
0.998 g/mL at 25 °C (lit.)
vapor pressure 
0.21Pa at 25℃
FEMA 
3408 | METHYL DIHYDROJASMONATE
refractive index 
n20/D 1.459(lit.)
Flash point:
>230 °F
storage temp. 
2-8°C
solubility 
H2O: insoluble
form 
Oil
color 
Clear Colorless
Odor
at 100.00 %. floral oily jasmin green lactonic tropical natural
Odor Type
floral
Water Solubility 
399.8mg/L(25 ºC)
JECFA Number
1898
Merck 
14,6052
InChIKey
KVWWIYGFBYDJQC-GHMZBOCLSA-N
LogP
2.93 at 22℃
CAS DataBase Reference
24851-98-7(CAS DataBase Reference)
NIST Chemistry Reference
Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester(24851-98-7)
EPA Substance Registry System
Methyl 3-oxo-2-pentyl-cyclopentaneacetate (24851-98-7)
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Safety

Safety Statements 
23-24/25
WGK Germany 
2
RTECS 
GY2453800
HS Code 
29183000
Toxicity
LD50 (g/kg): >5 orally in rats; >5 dermally in rabbits (Food Chem. Toxicol.)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W340804
Product name
Methyl dihydrojasmonate, mixture of cis and trans
Purity
≥96%, FG
Packaging
sample-k
Price
$54.6
Updated
2024/03/01
Sigma-Aldrich
Product number
W340804
Product name
Methyl dihydrojasmonate, mixture of cis and trans
Purity
≥96%, FG
Packaging
1kg
Price
$160
Updated
2024/03/01
Sigma-Aldrich
Product number
W340804
Product name
Methyl dihydrojasmonate, mixture of cis and trans
Purity
≥96%, FG
Packaging
5kg
Price
$423
Updated
2024/03/01
Sigma-Aldrich
Product number
W340804
Product name
Methyl dihydrojasmonate, mixture of cis and trans
Purity
≥96%, FG
Packaging
10Kg
Price
$711
Updated
2024/03/01
Sigma-Aldrich
Product number
59677
Product name
Methyl dihydrojasmonate, mixture of cis and trans
Purity
analytical standard
Packaging
1ml
Price
$63.9
Updated
2024/03/01
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Methyl dihydrojasmonate Chemical Properties,Usage,Production

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

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

Chemical Properties

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

Non flammable

Trade name

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

Methyl dihydrojasmonate Preparation Products And Raw materials

Raw materials

Cyclopentanone Valeraldehyde

Preparation Products

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Methyl dihydrojasmonate Suppliers

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View Lastest Price from Methyl dihydrojasmonate manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Methyl dihydrojasmonate 24851-98-7
Price
US $78.00-35.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-20
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Methyl dihydrojasmonate 24851-98-7
Price
US $0.00/Kg/Drum
Min. Order
200Kg/Drum
Purity
N/A
Supply Ability
80tons/month
Release date
2021-06-08
Hebei Yanxi Chemical Co., Ltd.
Product
HEDIONE 24851-98-7
Price
US $1.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20tons
Release date
2023-09-07

24851-98-7, Methyl dihydrojasmonateRelated Search:

Benzyl acetate Methyl methoxyacetate Magnesium acetate Ethyl acetate Methanol Butyl acetate Methyl glycolate Methyl benzoylformate PICROLONIC ACID Acetonitrile Kresoxim-methyl Vinyl acetate Methyl acrylate Ammonium acetate Sodium acetate Methyl pyruvate 2-Pentyl-3-methyl-2-cyclopenten-1-one CYCLOPENTYLMAGNESIUM CHLORIDE

  • 3-oxo-2-pentyl-cyclopentaneaceticacimethylester
  • (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%
  • Methyl dihydrojasmonate(EDC)
  • Nano Liposomal sodium tetrahydrojasmonate
  • 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
  • methyl dihydrojasmonate/Hedione
  • Einecs 246-495-9
  • Fema no. 3408
  • (±)-9,10-DIHYDROJASMONIC ACID METHYL ESTER (MeDJA)
  • Methyl DihydrojasMonate&nbsp
  • 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 (<i>cis-</i>and <i>trans-</i>Mixture)
  • Methyl dihydrojasmonate, mixture of cis and trans
  • Methyl dihydrojasmonate Methyl (3-oxo-2-pentylcyclopentyl)acetate
  • kharismal
  • methyl(2-pentyl-3-oxocyclopentyl)acetate
  • Methyl Dihydrojasmonate (cis- and trans- mixture)&gt
  • Methyl dihydrojasmonate(EDC),≥98%
  • Methyl dihydrojasmonate USP/EP/BP
  • MDJ
  • Hedione (methyl dihydrojasmonate, mdj)
  • C13H22O3 Methyl dihydrojasmonate 24851-98-7
  • Polymaleic acid 26099-09-2
  • Methyl dihydrojasmonate (mixture of isomers)
  • Methyldihydrojasmonate(mixtureofcis-andtrans-isomers
  • High Cis Hedione
  • Methyl dihydrojasmonate in isooctane
  • 24851-98-7