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24851-98-7

Basic Information
CAS No.: 24851-98-7
Name: Methyl dihydrojasmonate
Article Data: 36
Molecular Structure:
Molecular Structure of 24851-98-7 (Methyl dihydrojasmonate)
Formula: C13H22O3
Molecular Weight: 226.316
Synonyms: Cyclopentaneaceticacid, 3-oxo-2-pentyl-, methyl ester;Kharismal;Methyl (2-pentyl-3-oxocyclopentyl)acetate;Methyl(3-oxo-2-pentylcyclopentyl)acetate;methyl dihydrojasmonate (MDJ);Hedione;
EINECS: 246-495-9
Density: 0.984 g/cm3
Boiling Point: 307.8 °C at 760 mmHg
Flash Point: 130.8 °C
Solubility: insoluble in water
Appearance: Colorless clear liquid
Safety: 23-24/25
PSA: 43.37000
LogP: 2.72510
Synthetic route
24863-70-5

(3-oxo-2-pentyl-cyclopent-1-enyl)-acetic acid methyl ester

24851-98-7

methyl 3-oxo-2-pentylcyclopentaneacetate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In cyclohexane at 20℃; under 760 Torr; for 1.5h;100%
51806-23-6

methyl 1-carboxymethyl-1-(2-pentyl-3-oxocyclopentyl)acetate

24851-98-7

methyl 3-oxo-2-pentylcyclopentaneacetate

Conditions
ConditionsYield
With water at 190℃; for 3h; Inert atmosphere;97.82%
With methanol; water at 180℃; for 4h; Inert atmosphere;85%
With water at 215℃; for 4h;
51806-23-6

methyl 1-carboxymethyl-1-(2-pentyl-3-oxocyclopentyl)acetate

A

67-56-1

methanol

B

24851-98-7

methyl 3-oxo-2-pentylcyclopentaneacetate

Conditions
ConditionsYield
With water at 180 - 215℃; for 3.75 - 15h; Product distribution / selectivity;A n/a
B 93.5%
51806-23-6

methyl 1-carboxymethyl-1-(2-pentyl-3-oxocyclopentyl)acetate

A

24851-98-7

methyl 3-oxo-2-pentylcyclopentaneacetate

B

3572-64-3

2-(3-oxo-2-pentylcyclopentyl)acetic acid

Conditions
ConditionsYield
With water at 180 - 215℃; for 4 - 16h; Product distribution / selectivity;A 90.7%
B n/a
1101843-02-0

methyl jasmonate

24851-98-7

methyl 3-oxo-2-pentylcyclopentaneacetate

Conditions
ConditionsYield
With hydrogen; [(C6Me6)2Ru2(PPh2)H2][BF4] In ethanol at 60℃; under 37503 Torr; for 24h;90%
With 10% Pd/C; hydrogen
25564-22-1

2-pentyl-2-cyclopenten-1-one

108-59-8

malonic acid dimethyl ester

24851-98-7

methyl 3-oxo-2-pentylcyclopentaneacetate

Conditions
ConditionsYield
Stage #1: 2-pentyl-2-cyclopenten-1-one; malonic acid dimethyl ester With sodium methylate In methanol at 0℃; for 5h; Michael addition;
Stage #2: In water at 215℃; for 4h;
28%
Stage #1: 2-pentyl-2-cyclopenten-1-one; malonic acid dimethyl ester With sodium methylate In methanol at 0℃; for 5h; Michael Condensation;
Stage #2: at 215℃; for 4h;
3572-64-3

2-(3-oxo-2-pentylcyclopentyl)acetic acid

24851-98-7

methyl 3-oxo-2-pentylcyclopentaneacetate

Conditions
ConditionsYield
Yield given;
694528-26-2

2-(1-hydroxypentyl)cyclopent-2-en-1-one

1445-45-0

Trimethyl orthoacetate

24851-98-7

methyl 3-oxo-2-pentylcyclopentaneacetate

Conditions
ConditionsYield
Stage #1: 2-(1-hydroxypentyl)cyclopent-2-en-1-one; Trimethyl orthoacetate With Trimethylacetic acid at 110℃; for 3h; Claisen rearrangement;
Stage #2: With hydrogen; palladium on activated charcoal In cyclohexane at 0℃; under 760 Torr; for 18h;
110-53-2

1-Bromopentane

24851-98-7

methyl 3-oxo-2-pentylcyclopentaneacetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 83 percent
2: 87 percent / PPh3 / Pd(OAc)2 / various solvent(s) / 3 h / Heating
3: 88 percent / NaI / hexamethylphosphoric acid triamide / 100 °C
4: 9-BBN
5: CrO3
View Scheme
Multi-step reaction with 4 steps
1: ammonia; sodium / -40 - 20 °C
2: di(rhodium)tetracarbonyl dichloride; 4-methylmorpholine N-oxide / 30 h / 80 °C / 3750.38 - 37503.8 Torr / Glovebox; Autoclave
3: sodium methylate / methanol / 2 h / -5 °C / Inert atmosphere
4: water; methanol / 4 h / 180 °C / Inert atmosphere
View Scheme

3-Hydroxymethyl-2-pentyl-cyclopentanol

24851-98-7

methyl 3-oxo-2-pentylcyclopentaneacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CrO3
View Scheme
Downstream Products
3572-64-3
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Chemistry

Molecule structure of Hedione (CAS NO.24851-98-7):

IUPAC Name: Methyl 2-(3-oxo-2-pentylcyclopentyl)acetate 
Molecular Weight: 226.31198 g/mol
Molecular Formula: C13H22O3 
Density: 0.984 g/cm3 
Boiling Point: 307.8 °C at 760 mmHg 
Flash Point: 130.8 °C
Index of Refraction: 1.453
Molar Refractivity: 62.14 cm3
Molar Volume: 229.8 cm3 
Surface Tension: 32.2 dyne/cm 
Enthalpy of Vaporization: 54.84 kJ/mol
Vapour Pressure: 0.00071 mmHg at 25 °C 
Water solubility: insoluble
XLogP3-AA: 2.7
H-Bond Acceptor: 3
Rotatable Bond Count: 7
Tautomer Count: 3
Exact Mass: 226.156895
MonoIsotopic Mass: 226.156895
Topological Polar Surface Area: 43.4
Heavy Atom Count: 16
Canonical SMILES: CCCCCC1C(CCC1=O)CC(=O)OC
InChI: InChI=1S/C13H22O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h10-11H,3-9H2,1-2H3
InChIKey: KVWWIYGFBYDJQC-UHFFFAOYSA-N
EINECS: 246-495-9
Product Categories: Alphabetical Listings;Flavors and Fragrances;M-N

Uses

 Hedione is commonly used as synthesis spice, and it is commonly used in the preparation of jasmine, lily of the valley, and  east type essence. It can be both applicated in cosmetics and food.

Toxicity Data With Reference

1.    

orl-rat LD50:>5 g/kg

    FCTOD7    Food and Chemical Toxicology. 30 (1992),85S.
2.    

skn-rbt LDLo:5 g/kg

    FCTOD7    Food and Chemical Toxicology. 30 (1992),85S.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Safety Statements: 23-24/25 
S23:Do not breathe vapour. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: GY2453800
Low toxicity by ingestion and skin contact. When heated to decomposition it emits acrid smoke and irritating vapors.

Specification

 Hedione (CAS NO.24851-98-7) is also named as Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester ; FEMA No. 3408 ; Kharismal ; Methyl (2-pentyl-3-oxocyclopentyl)acetate ; Methyl (3-oxo-2-pentylcyclopentyl)acetate ; Methyl 3-oxo-2-pentyl-cyclopentaneacetate ; Methyl 3-oxo-2-pentylcyclopentaneacetate ; Methyl dihydrojasmonate . Hedione (CAS NO.24851-98-7) is pale straw yellow to yellow transparent oily liquid. It is an ester and a diffusive aroma compound, with the smell vaguely similar to jasmine.