488-10-8

Basic information

• Product Name: Jasmone
• Synonyms: 3-METHYL-2-(CIS-2-PENTENYL)-2-CYCLOPENTEN-1-ONE;3-METHYL-2-(2-PENTENYL)-2-CYCLOPENTEN-1-ONE;CIS-JASMONE;CIS-3-METHYL-2-(2-PENTENYL)-2-CYCLOPENTEN-1-ONE;FEMA 3196;JASMONE;JASMONE, CIS-;(Z)-JASMONE
• CAS NO: 488-10-8
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.25
• EINECS: 207-668-4
• Product Categories: ketone Flavor
• Mol File: 488-10-8.mol
• Article Data: 48

Chemical Properties

• Boiling Point: 134-135 °C12 mm Hg(lit.)
• Flash Point: 225 °F
• Appearance: COA
• Density: 0.94 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0567mmHg at 25°C
• Refractive Index: n20/D 1.498(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 1.48g/L at 20℃
• Merck: 14,5259
• BRN: 1907713
• CAS DataBase Reference: Jasmone(CAS DataBase Reference)
• NIST Chemistry Reference: Jasmone(488-10-8)
• EPA Substance Registry System: Jasmone(488-10-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 2
• RTECS: GY7301000
• TSCA: Yes
• Hazardous Substances Data: 488-10-8(Hazardous Substances Data)

Usage

Description

This has a jasmine odor.

Chemical Properties

Jasmone has a floral, fruity, jasmine odor. cis-Jasmone is widely used in the creation of high quality florals like jasmine and tuberose. Also used in the reconstitution of synthetic essential oils.

Occurrence

The cis-form is reportedly occurring naturally; it is found in the essential oils of jasmine (3%), jonquil, and Pittosporum glabratum, in neroli oil, in peppermint (Mentha piperita), and in bergamot, apricot, raspberry, cinnamon, corn mint and spearmint oils, beer, tea, soybean and heated beans.

Uses

Perfumery.

Definition

A ketone found in jasmine oil and other flower oils.

Taste threshold values

Taste characteristics at 25 ppm: woody, bitter, tea, with a citrus and floral nuance.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 2317, 1974 DOI: 10.1021/jo00929a053Synthetic Communications, 5, p. 1, 1975 DOI: 10.1080/00397917508063507

Flammability and Explosibility

Notclassified

Synthesis

A review and classification on the synthesis of jasmone is available.

InChI:InChI=1/C10H14O/c1-3-4-5-9-8(2)6-7-10(9)11/h3-4H,5-7H2,1-2H3/b4-3-

Synthetic route

3-methyl-2-(2-pentynyl)-2-cyclopentenone (7051-37-8) → cis-jasmone (488-10-8)

Conditions	Yield
With hydrogen; Lindlar's catalyst In hexane	97%
With hydrogen; Lindlar's catalyst In ethyl acetate under 760 Torr;	95%
With hydrogen; Lindlar's catalyst In hexane	90%
With hydrogen; Lindlar's catalyst In ethanol	65%
Yield given;

3-bromo-2-<(Z)-2-pentenyl>-2-cyclopenten-1-one (82909-46-4) + lithium dimethylcuprate → cis-jasmone (488-10-8)

Conditions	Yield
In diethyl ether 1.) -78 degC, 10 min., 2.) 0 degC, 1 h;	93%

undec-8c-ene-2,5-dione (4868-21-7) → cis-jasmone (488-10-8)

Conditions	Yield
With sodium hydroxide In ethanol for 4h; Heating;	92%
With potassium hydroxide In ethanol for 2h; Heating;	91%
With sodium hydroxide; water	88%

2-(2-cis-pentenyl)-3-methyl-5-(phenylthio)-2-cyclopenten-1-one (128192-01-8) → cis-jasmone (488-10-8)

Conditions	Yield
With nickel In acetone	88%
With nickel

methyl (Z)-2-<4-<(diethoxyphosphoryl)oxy>-1-oxo-4-pentenyl>-4-heptenoate (106763-43-3) → cis-jasmone (488-10-8)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 80℃; for 20h;	87%

4-methyl-5-(2-pentenyl)cyclopent-2-en-1-one (32556-66-4, 32556-68-6, 87392-23-2, 131321-83-0, 135029-97-9, 135029-98-0) → cis-jasmone (488-10-8)

Conditions	Yield
With sodium methylate In methanol Ambient temperature;	83%

ethyl (Z)-3-oxo-2-(2-oxopropyl)-6-nonenoate → cis-jasmone (488-10-8)

Conditions	Yield
With potassium hydroxide In ethanol at 95℃; for 0.5h;	76%

2-((4R,5S)-5-Ethyl-2-methoxy-[1,3]dioxolan-4-ylmethyl)-3-methyl-cyclopent-2-enone → cis-jasmone (488-10-8)

Conditions	Yield
In acetic anhydride for 6h; Heating;	75%

1-methyl-2-pent-2-enyl-cyclopent-2-enol (207798-52-5) → cis-jasmone (488-10-8)

Conditions	Yield
With dipyridinium dichromate In dichloromethane at 0℃; for 1h;	74%

2-(cis-2-Pentenyl)-3-<(phenylsulfonyl)methyl>-2-cyclopenten-1-one (132604-79-6) → cis-jasmone (488-10-8)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 1h; Heating;	71%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating; Yield given;

(Z)-3-methyl-2-(pent-2-enyl)cyclopent-2-enol (165590-85-2) → cis-jasmone (488-10-8)

Conditions	Yield
With jones reagent In acetone	62%

undec-8c-ene-2,5-dione (4868-21-7) → cis-jasmone (488-10-8) + trans-jasmone (6261-18-3)

Conditions	Yield
With aluminum oxide In benzene for 3h; Heating;	A 60% B n/a

ethene (74-85-1) + hexacarbonyl(oct-4(Z)-en-1-yne)dicobalt → cis-jasmone (488-10-8)

Conditions	Yield
In toluene under 22800 Torr; for 36h; Heating;	22%

1-(pent-2'-enyl)-5-methyl-6-oxabicyclo[3.1.0]hexan-2-one → cis-jasmone (488-10-8)

Conditions	Yield
With decane; TEA In acetonitrile for 120h; Irradiation;	15%

3-chloro-2-<(diethoxyphosphoryl)oxy>-1-propene (81431-81-4) + 2-acetyl-(Z)-hept-4-enoic acid methyl ester (68776-91-0) → cis-jasmone (488-10-8)

Conditions	Yield
With n-butyllithium; sodium hydride 1.) hexane, from 0 to 23 deg C, 20 min, 2.) hexane, from 0 to 23 deg C, 1 h 10 min; Yield given. Multistep reaction;

(Z)-3-hexenyl iodide (21676-03-9) + (N-methylanilino)prop-2-enenitrile (69567-06-2) + N-isopropyliden-cyclohexyl amine (6407-36-9) → cis-jasmone (488-10-8)

Conditions	Yield
With hydrogenchloride; natronlauge; lithium diisopropyl amide Yield given. Multistep reaction;

(Z)-2-(2-pentenyl)-2-cyclopenten-1-one (41031-88-3) + methyllithium (917-54-4) → cis-jasmone (488-10-8)

Conditions	Yield
With chromium(VI) oxide

2-Formylmethyl-3-methyl-2-cyclopenten-1-one (58282-77-2) + n-propyltriphenylphosphonium bromide (6228-47-3) → cis-jasmone (488-10-8)

Conditions	Yield
With n-butyllithium 1.) THF-hexane, RT, 1 h, 2.) THF, -10 deg C, 1.5 h; Yield given. Multistep reaction;

ethyl 2-methyl-1-(2-pentyn-1-yl)-3-cyclopenten-5-one-1-carboxylate (53376-48-0) → cis-jasmone (488-10-8)

Conditions	Yield
With sodium chloride In dimethyl sulfoxide at 160℃;

(4R,5S)-4-Methyl-5-((E)-pent-2-enyl)-cyclopent-2-enone (32556-66-4, 32556-68-6, 87392-23-2, 131321-83-0, 135029-97-9, 135029-98-0) → cis-jasmone (488-10-8) + trans-jasmone (6261-18-3)

Conditions	Yield
With Amberlite IRA-400 In methanol for 24h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

N-[1-ethoxycarbonyl-3-(3-indolyl)propyl]-L-alanyl-L-proline (79155-17-2) → cis-jasmone (488-10-8)

Conditions	Yield
With diethylamine In chloroform Heating;

4-Methyl-3-((Z)-pent-2-enyl)-1,2-bis-trimethylsilanyloxy-cyclopentene (73959-78-1) → cis-jasmone (488-10-8)

Conditions	Yield
With phosphoric acid; toluene-4-sulfonic acid 1.) 60 deg C, 3 h, 2.) DMF, 60 deg C, 20 h; Yield given. Multistep reaction;

ethylmagnesium bromide (925-90-6) + 2-methylene-3-methyl-3-methoxy-methyloxycyclopentanone (79858-12-1) + acetylene (74-86-2) → cis-jasmone (488-10-8)

Conditions	Yield
With copper(l) iodide Yield given. Multistep reaction;

(+-)-2.5-dioxo-undecene-(8c)-carboxylic acid-(4)-methyl ester → cis-jasmone (488-10-8)

Conditions	Yield
With sodium hydroxide

1-methyl-2-c.4)-yl>-cyclopenten-(1)-one-(3) → cis-jasmone (488-10-8)

Conditions	Yield
With hydrogen bromide; acetic acid anschliessend Erwaermen mit Zink-Pulver;

4-hydroxy-4-methyl-5-ethoxycarbonyl-decen-(7c)-oic acid (1)-lactone → cis-jasmone (488-10-8)

Conditions	Yield
With hydrogenchloride at 0℃; Behandeln des Reaktionsprodukts mit Natrium in Xylol und anschliessendem Erhitzen mit wss. H2SO4;

5-hydroxy-1-methyl-2--cyclopenten-(1)-one-(3) → cis-jasmone (488-10-8)

Conditions	Yield
With diethyl ether; aluminium amalgam; water

tert-butyl-dimethyl-(3-methyl-2-pent-2-enyl-cyclopent-2-enyloxy)-silane (892145-35-6) → cis-jasmone (488-10-8)

cis-jasmone (488-10-8) → (Z)-3-methyl-2-(pent-2-enyl)cyclopent-2-enol (165590-85-2)

Conditions	Yield
With lithium pyrrolidinoborohydride at 25℃;	98%
With LiPyrrBH3 In tetrahydrofuran at 25℃; for 3h;	98%
With sodium tetrahydroborate; calcium chloride In methanol 1a) 30 min, 25 deg C, 1b) 0 deg C, 1 h;	93%

cis-jasmone (488-10-8) → dihydro-cis-jasmone (1128-08-1)

Conditions	Yield
With hydrogen; SC-1 Ni2B In methanol at 25℃; under 760 Torr; for 24h;	97%
With hydrogen; palladium In methanol at 20℃; for 19h;	60%
With hydrogen; [(C6Me6)2Ru2(PPh2)H2][BF4] In ethanol at 60℃; under 37503 Torr; for 24h;	47%

cis-jasmone (488-10-8) + acetic acid (64-19-7) → C13H18O3

Conditions	Yield
With oxygen; copper diacetate; palladium diacetate; p-benzoquinone at 90℃; under 7600.51 Torr; for 2h; Kinetics; Temperature;	87%

cis-jasmone (488-10-8) + trimethylaluminum (75-24-1) → cis-2-(2-penten-1-yl)-3,3-dimethylcyclopentanone (157562-89-5)

Conditions	Yield
With bis(acetylacetonate)nickel(II) In tetrahydrofuran; hexane for 4h; Ambient temperature;	85%

cis-jasmone (488-10-8) → 3-methyl-2-(2-cis-pentenyl)cyclopentanone (7051-39-0, 82768-42-1, 82768-43-2)

Conditions	Yield
With sodium t-butanolate; poly(methylhydrosiloxane); 1,3-bis(2,6-diisopropylphenyl)imidazolium copper(I) chloride In toluene at 20℃; for 1h;	85%

cis-jasmone (488-10-8) → 2-[(2RS,3RS)-2,3-dihydroxypentyl]-3-methylcyclopent-2-enone

Conditions	Yield
With Fe(bpmen)(OTf)2; dihydrogen peroxide; acetic acid In acetonitrile at 20℃; Concentration;	80%

cis-jasmone (488-10-8) → 2-((2S,3S)-2,3-Dihydroxy-pentyl)-3-methyl-cyclopent-2-enone (107046-58-2, 107046-59-3, 148694-04-6)

Conditions	Yield
With N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamineiron(II) bis(triflate); dihydrogen peroxide In acetonitrile at 20℃; for 0.166667h; Catalytic behavior; stereoselective reaction;	80%

formaldehyd (50-00-0) + cis-jasmone (488-10-8) → (Z)-3-methyl-5-methylene-2-(pent-2-en-1-yl)cyclopent-2-en-1-one

Conditions	Yield
With magnesium sulfate; trifluoroacetic acid; diisopropylamine 2,2,2-trifluoroacetic acid salt In tetrahydrofuran at 60℃; for 24h;	80%

cis-jasmone (488-10-8) + methyllithium (917-54-4) → cis-2-(2-penten-1-yl)-3,3-dimethylcyclopentanone (157562-89-5)

Conditions	Yield
With copper(l) iodide; boron trifluoride diethyl etherate In diethyl ether at -78 - 20℃; for 4h;	63%

cis-jasmone (488-10-8) + trimethylsulfoxonium iodide (1774-47-6) → 5-methyl-1-(pent-2'-enyl)bicyclo<3.1.0>hexan-2-one

Conditions	Yield
With sodium hydride In dimethyl sulfoxide for 4h; Ambient temperature;	54%

cis-jasmone (488-10-8) → 2-(2,3-dibromobutyl)-3-methylcyclopent-2-enone (51615-66-8)

Conditions	Yield
With hydrogen bromide; dimethyl sulfoxide In chloroform; water at 20℃; for 24h;	50%

cis-jasmone (488-10-8) → 1-(pent-2'-enyl)-5-methyl-6-oxabicyclo[3.1.0]hexan-2-one

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In methanol for 3h; Ambient temperature;	47%

cis-jasmone (488-10-8) → (1'R*,2'R*)-2-(2'-ethylcyclopropyl)-3-methyl-2-cyclopenten-1-one + (1'S*,2'R*)-2-(2'-ethylcyclopropyl)-3-methyl-2-cyclopenten-1-one

Conditions	Yield
In ethyl acetate for 20h; Irradiation;	A 42% B 29%

cis-jasmone (488-10-8) → 2-[(2SR,3RS)-2,3-dihydroxypentyl]-3-methylcyclopent-2-enone (107046-58-2, 107046-59-3, 148694-04-6) + 2-((2S,3S)-2,3-Dihydroxy-pentyl)-3-methyl-cyclopent-2-enone (107046-58-2, 107046-59-3, 148694-04-6)

Conditions	Yield
With [Fe(CF3SO3)2(1-[2′-(6'-methylpyridyl)methyl]-4,7-dimethyl-1,4,7-triazacyclononane)]; water; dihydrogen peroxide In acetonitrile at 0℃; for 0.5h; Green chemistry; chemoselective reaction;	A 34% B 9%

cis-jasmone (488-10-8) → 2-((E)-3-Hydroxy-pent-1-enyl)-3-methyl-cyclopent-2-enone + 2-((E)-2-Hydroxy-pent-3-enyl)-3-methyl-cyclopent-2-enone + 2-((E)-3-Hydroperoxy-pent-1-enyl)-3-methyl-cyclopent-2-enone + 2-((E)-2-Hydroperoxy-pent-3-enyl)-3-methyl-cyclopent-2-enone

Conditions	Yield
With oxygen; rose bengal In methanol for 20h; Irradiation;	A 5% B 5% C 30% D 18%

cis-jasmone (488-10-8) → C11H18O4 + 2-((2S,3S)-2,3-Dihydroxy-pentyl)-3-methyl-cyclopent-2-enone (107046-58-2, 107046-59-3, 148694-04-6)

Conditions	Yield
With oxone; [Fe(tris(2-pyridyl)amine)(triflate)2] In water; acetonitrile at 8℃; for 6h; stereoselective reaction;	A 30% B 30%

Upstream product

• 41031-88-3 (Z)-2-(2-pentenyl)-2-cyclopenten-1-one 
• 917-54-4 methyllithium 
• 7051-37-8 3-methyl-2-(2-pentynyl)-2-cyclopentenone 
• 73959-78-1 4-Methyl-3-((Z)-pent-2-enyl)-1,2-bis-trimethylsilanyloxy-cyclopentene 
• 165590-85-2 (Z)-3-methyl-2-(pent-2-enyl)cyclopent-2-enol 
• 34498-11-8 1-iodo-2-pentyne 
• 1576-95-0 cis-2-penten-1-ol 
• 156937-64-3 methanesulfonic acid pent-2-enyl ester 
• 1113-77-5 2-acetyl-3-methyl-succinic acid diethyl ester 
• 21676-03-9 (Z)-3-hexenyl iodide 
• 16400-32-1 1-bromo-pent-2-yne 
• 7051-43-6 undec-8-yne-2,5-dione 
• 94127-07-8 2-acetyl-(2'-pent-β-ynyl)-4-methyl-butyrolactone 
• 79503-95-0 methanesulfonic acid hex-3(Z)-enyl ester 

Downstream Products

• 1128-08-1 dihydro-cis-jasmone 
• 23260-40-4 5-Methyl-5-cyclopenten-2-one-1-ylcarboxylic acid 
• 123-76-2 levulinic acid 
• 148694-04-6 2-(2',3'-Dihydroxypentan-1'-yl)-3-methyl-2-cyclopenten-1-one 
• 6261-18-3 trans-jasmone 
• 515178-90-2 (2S,6R)-2-((1R,2R)-2-Ethyl-cyclopropylmethyl)-6-hydroxy-3,3-dimethyl-cyclohexanone 
• 5009-20-1 3-Methyl-2-(2-cis-pentenyl)-2-cyclopentenone (cis-Jasmone) 2,4-dinitrophenylhydrazone 
• 108-24-7 acetic anhydride 

Relevant articles and documents

1,2-Bisanionic coupling approach to 2,3-disubstituted cyclopentenols and cyclopentenones

We describe a new approach to 2,3-disubstituted cyclopentenols and cyclopentenones through two consecutive regioselective additions of equal or different electrophiles to a cyclopentene bisanionic synthon. Indeed, on exposure to BuLi, 3-bromo-2-iodocyclopent-2-enol O-TBS ether undergoes iodine-lithium permutation with complete regioselectivity. Successive reaction of the monolithium anion with different C(sp2)- and C(sp 3)-electrophiles affords the corresponding 2-substituted-3- bromocyclopentenol derivative. Subsequent bromo-lithium exchange with t-BuLi, followed by reaction with an equal or different electrophile, affords the desired 2,3-disubstituted cyclopentenol.

Synthesis of Pyrethroids and Jasmonoids through Palladium-Catalyzed Cross-Coupling Reactions

The synthesis of jasmone and related jasmonoids and pyrethroids is described. These compounds play a defensive role in plants and share a common cyclopentenone core with variations in the side chains. Jasmone, cinerone, allylrethrone, and derivatives were synthesized through -allyl palladium cross-coupling of stannane derivatives. With selective hydrogenation, dihydrojasmone, and dihydrocinerone were also synthesized.

Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone

Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.