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488-10-8

Basic Information
CAS No.: 488-10-8
Name: Jasmone
Molecular Structure:
Molecular Structure of 488-10-8 (Jasmone)
Formula: C11H16O
Molecular Weight: 164.27
Synonyms: 2-Cyclopenten-1-one,3-methyl-2-(2-pentenyl)-, (Z)- (8CI);2-Cyclopenten-1-one,3-methyl-2-(2Z)-2-pentenyl- (9CI);Jasmone (6CI);(Z)-Jasmone;3-Methyl-2-(2-cis-pentenyl)-2-cyclopenten-1-one;3-Methyl-2-(cis-2-pentenyl)-2-cyclopenten-1-one;cis-Jasmone;
EINECS: 207-668-4
Density: 0.937 g/cm3
Melting Point: 203 - 205oC
Boiling Point: 264.2 °C at 760 mmHg
Flash Point: 107.2 °C
Solubility:
Appearance: COA
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 17.07000
LogP: 3.02210
Synthetic route
7051-37-8

3-methyl-2-(2-pentynyl)-2-cyclopentenone

488-10-8

cis-jasmone

Conditions
ConditionsYield
With hydrogen; Lindlar's catalyst In hexane97%
With hydrogen; Lindlar's catalyst In ethyl acetate under 760 Torr;95%
With hydrogen; Lindlar's catalyst In hexane90%
With hydrogen; Lindlar's catalyst In ethanol65%
Yield given;
82909-46-4

3-bromo-2-<(Z)-2-pentenyl>-2-cyclopenten-1-one

lithium dimethylcuprate

lithium dimethylcuprate

488-10-8

cis-jasmone

Conditions
ConditionsYield
In diethyl ether 1.) -78 degC, 10 min., 2.) 0 degC, 1 h;93%
4868-21-7

undec-8c-ene-2,5-dione

488-10-8

cis-jasmone

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 4h; Heating;92%
With potassium hydroxide In ethanol for 2h; Heating;91%
With sodium hydroxide; water88%
128192-01-8

2-(2-cis-pentenyl)-3-methyl-5-(phenylthio)-2-cyclopenten-1-one

488-10-8

cis-jasmone

Conditions
ConditionsYield
With nickel In acetone88%
With nickel
106763-43-3

methyl (Z)-2-<4-<(diethoxyphosphoryl)oxy>-1-oxo-4-pentenyl>-4-heptenoate

488-10-8

cis-jasmone

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 80℃; for 20h;87%
488-10-8

cis-jasmone

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

ethyl (Z)-3-oxo-2-(2-oxopropyl)-6-nonenoate

488-10-8

cis-jasmone

Conditions
ConditionsYield
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

488-10-8

cis-jasmone

Conditions
ConditionsYield
In acetic anhydride for 6h; Heating;75%
207798-52-5

1-methyl-2-pent-2-enyl-cyclopent-2-enol

488-10-8

cis-jasmone

Conditions
ConditionsYield
With dipyridinium dichromate In dichloromethane at 0℃; for 1h;74%
132604-79-6

2-(cis-2-Pentenyl)-3-<(phenylsulfonyl)methyl>-2-cyclopenten-1-one

488-10-8

cis-jasmone

Conditions
ConditionsYield
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;
165590-85-2

(Z)-3-methyl-2-(pent-2-enyl)cyclopent-2-enol

488-10-8

cis-jasmone

Conditions
ConditionsYield
With jones reagent In acetone62%
4868-21-7

undec-8c-ene-2,5-dione

A

488-10-8

cis-jasmone

B

6261-18-3

trans-jasmone

Conditions
ConditionsYield
With aluminum oxide In benzene for 3h; Heating;A 60%
B n/a
74-85-1

ethene

hexacarbonyl(oct-4(Z)-en-1-yne)dicobalt

hexacarbonyl(oct-4(Z)-en-1-yne)dicobalt

488-10-8

cis-jasmone

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

1-(pent-2'-enyl)-5-methyl-6-oxabicyclo[3.1.0]hexan-2-one

488-10-8

cis-jasmone

Conditions
ConditionsYield
With decane; TEA In acetonitrile for 120h; Irradiation;15%
81431-81-4

3-chloro-2-<(diethoxyphosphoryl)oxy>-1-propene

68776-91-0

2-acetyl-(Z)-hept-4-enoic acid methyl ester

488-10-8

cis-jasmone

Conditions
ConditionsYield
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;
21676-03-9

(Z)-3-hexenyl iodide

69567-06-2

(N-methylanilino)prop-2-enenitrile

6407-36-9

N-isopropyliden-cyclohexyl amine

488-10-8

cis-jasmone

Conditions
ConditionsYield
With hydrogenchloride; natronlauge; lithium diisopropyl amide Yield given. Multistep reaction;
41031-88-3

(Z)-2-(2-pentenyl)-2-cyclopenten-1-one

917-54-4

methyllithium

488-10-8

cis-jasmone

Conditions
ConditionsYield
With chromium(VI) oxide
58282-77-2

2-Formylmethyl-3-methyl-2-cyclopenten-1-one

6228-47-3

n-propyltriphenylphosphonium bromide

488-10-8

cis-jasmone

Conditions
ConditionsYield
With n-butyllithium 1.) THF-hexane, RT, 1 h, 2.) THF, -10 deg C, 1.5 h; Yield given. Multistep reaction;
53376-48-0

ethyl 2-methyl-1-(2-pentyn-1-yl)-3-cyclopenten-5-one-1-carboxylate

488-10-8

cis-jasmone

Conditions
ConditionsYield
With sodium chloride In dimethyl sulfoxide at 160℃;
32556-66-4, 32556-68-6, 87392-23-2, 131321-83-0, 135029-97-9, 135029-98-0

(4R,5S)-4-Methyl-5-((E)-pent-2-enyl)-cyclopent-2-enone

A

488-10-8

cis-jasmone

B

6261-18-3

trans-jasmone

Conditions
ConditionsYield
With Amberlite IRA-400 In methanol for 24h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
79155-17-2

N-[1-ethoxycarbonyl-3-(3-indolyl)propyl]-L-alanyl-L-proline

488-10-8

cis-jasmone

Conditions
ConditionsYield
With diethylamine In chloroform Heating;
73959-78-1

4-Methyl-3-((Z)-pent-2-enyl)-1,2-bis-trimethylsilanyloxy-cyclopentene

488-10-8

cis-jasmone

Conditions
ConditionsYield
With phosphoric acid; toluene-4-sulfonic acid 1.) 60 deg C, 3 h, 2.) DMF, 60 deg C, 20 h; Yield given. Multistep reaction;
925-90-6

ethylmagnesium bromide

79858-12-1

2-methylene-3-methyl-3-methoxy-methyloxycyclopentanone

74-86-2

acetylene

488-10-8

cis-jasmone

Conditions
ConditionsYield
With copper(l) iodide Yield given. Multistep reaction;
(+-)-2.5-dioxo-undecene-(8c)-carboxylic acid-(4)-methyl ester

(+-)-2.5-dioxo-undecene-(8c)-carboxylic acid-(4)-methyl ester

488-10-8

cis-jasmone

Conditions
ConditionsYield
With sodium hydroxide
1-methyl-2-c.4)-yl>-cyclopenten-(1)-one-(3)

1-methyl-2-c.4)-yl>-cyclopenten-(1)-one-(3)

488-10-8

cis-jasmone

Conditions
ConditionsYield
With hydrogen bromide; acetic acid anschliessend Erwaermen mit Zink-Pulver;
4-hydroxy-4-methyl-5-ethoxycarbonyl-decen-(7c)-oic acid (1)-lactone

4-hydroxy-4-methyl-5-ethoxycarbonyl-decen-(7c)-oic acid (1)-lactone

488-10-8

cis-jasmone

Conditions
ConditionsYield
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)

5-hydroxy-1-methyl-2--cyclopenten-(1)-one-(3)

488-10-8

cis-jasmone

Conditions
ConditionsYield
With diethyl ether; aluminium amalgam; water
892145-35-6

tert-butyl-dimethyl-(3-methyl-2-pent-2-enyl-cyclopent-2-enyloxy)-silane

488-10-8

cis-jasmone

488-10-8

cis-jasmone

165590-85-2

(Z)-3-methyl-2-(pent-2-enyl)cyclopent-2-enol

Conditions
ConditionsYield
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%
488-10-8

cis-jasmone

1128-08-1

dihydro-cis-jasmone

Conditions
ConditionsYield
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%
488-10-8

cis-jasmone

64-19-7

acetic acid

C13H18O3

Conditions
ConditionsYield
With oxygen; copper diacetate; palladium diacetate; p-benzoquinone at 90℃; under 7600.51 Torr; for 2h; Kinetics; Temperature;87%
488-10-8

cis-jasmone

75-24-1

trimethylaluminum

157562-89-5

cis-2-(2-penten-1-yl)-3,3-dimethylcyclopentanone

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II) In tetrahydrofuran; hexane for 4h; Ambient temperature;85%
488-10-8

cis-jasmone

7051-39-0, 82768-42-1, 82768-43-2

3-methyl-2-(2-cis-pentenyl)cyclopentanone

Conditions
ConditionsYield
With sodium t-butanolate; poly(methylhydrosiloxane); 1,3-bis(2,6-diisopropylphenyl)imidazolium copper(I) chloride In toluene at 20℃; for 1h;85%
488-10-8

cis-jasmone

2-[(2RS,3RS)-2,3-dihydroxypentyl]-3-methylcyclopent-2-enone

Conditions
ConditionsYield
With Fe(bpmen)(OTf)2; dihydrogen peroxide; acetic acid In acetonitrile at 20℃; Concentration;80%
488-10-8

cis-jasmone

107046-58-2, 107046-59-3, 148694-04-6

2-((2S,3S)-2,3-Dihydroxy-pentyl)-3-methyl-cyclopent-2-enone

Conditions
ConditionsYield
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%
50-00-0

formaldehyd

488-10-8

cis-jasmone

(Z)-3-methyl-5-methylene-2-(pent-2-en-1-yl)cyclopent-2-en-1-one

Conditions
ConditionsYield
With magnesium sulfate; trifluoroacetic acid; diisopropylamine 2,2,2-trifluoroacetic acid salt In tetrahydrofuran at 60℃; for 24h;80%
488-10-8

cis-jasmone

917-54-4

methyllithium

157562-89-5

cis-2-(2-penten-1-yl)-3,3-dimethylcyclopentanone

Conditions
ConditionsYield
With copper(l) iodide; boron trifluoride diethyl etherate In diethyl ether at -78 - 20℃; for 4h;63%
488-10-8

cis-jasmone

1774-47-6

trimethylsulfoxonium iodide

5-methyl-1-(pent-2'-enyl)bicyclo<3.1.0>hexan-2-one

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide for 4h; Ambient temperature;54%
488-10-8

cis-jasmone

51615-66-8

2-(2,3-dibromobutyl)-3-methylcyclopent-2-enone

Conditions
ConditionsYield
With hydrogen bromide; dimethyl sulfoxide In chloroform; water at 20℃; for 24h;50%
488-10-8

cis-jasmone

1-(pent-2'-enyl)-5-methyl-6-oxabicyclo[3.1.0]hexan-2-one

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide In methanol for 3h; Ambient temperature;47%
488-10-8

cis-jasmone

(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
ConditionsYield
In ethyl acetate for 20h; Irradiation;A 42%
B 29%
488-10-8

cis-jasmone

107046-58-2, 107046-59-3, 148694-04-6

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

Conditions
ConditionsYield
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%
488-10-8

cis-jasmone

A

2-((E)-3-Hydroxy-pent-1-enyl)-3-methyl-cyclopent-2-enone

B

2-((E)-2-Hydroxy-pent-3-enyl)-3-methyl-cyclopent-2-enone

C

2-((E)-3-Hydroperoxy-pent-1-enyl)-3-methyl-cyclopent-2-enone

D

2-((E)-2-Hydroperoxy-pent-3-enyl)-3-methyl-cyclopent-2-enone

Conditions
ConditionsYield
With oxygen; rose bengal In methanol for 20h; Irradiation;A 5%
B 5%
C 30%
D 18%
488-10-8

cis-jasmone

A

C11H18O4

107046-58-2, 107046-59-3, 148694-04-6

2-((2S,3S)-2,3-Dihydroxy-pentyl)-3-methyl-cyclopent-2-enone

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

Molecule structure of Jasmone (CAS NO.488-10-8):

IUPAC Name: 3-Methyl-2-[(Z)-pent-2-enyl]cyclopent-2-en-1-one 
Molecular Weight: 164.24414 g/mol
Molecular Formula: C11H16
Density: 0.937 g/cm3 
Boiling Point: 264.2 °C at 760 mmHg 
Flash Point: 107.2 °C
Index of Refraction: 1.491
Molar Refractivity: 50.77 cm3
Molar Volume: 175.1 cm3
Polarizability: 20.12×10-24 cm3
Surface Tension: 31.1 dyne/cm 
Enthalpy of Vaporization: 50.21 kJ/mol
Vapour Pressure: 0.00982 mmHg at 25 °C
XLogP3-AA: 2.2
H-Bond Acceptor: 1
Rotatable Bond Count: 3
Tautomer Count: 10
Exact Mass: 164.120115
MonoIsotopic Mass: 164.120115
Topological Polar Surface Area: 17.1
Heavy Atom Count: 12
Complexity: 233
Canonical SMILES: CCC=CCC1=C(CCC1=O)C
Isomeric SMILES: CC/C=C\CC1=C(CCC1=O)C
InChI: InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-
InChIKey: XMLSXPIVAXONDL-PLNGDYQASA-N
EINECS: 207-668-4
Product Categories: ketone Flavor

Uses

 Jasmone (CAS NO.488-10-8) can act as an attractant or a repellent for various insects. However it is used primarily in perfumes and cosmetics. It also can be used in jasmine and mint flavor.

Production

  Jasmone is manufactured within plants by the metabolism of jasmonate, from linolenic acid by the octadecanoid pathway.

Toxicity Data With Reference

1.    

skn-rbt 500 mg/24H MOD

    FCTXAV    Food and Cosmetics Toxicology. 17 (1979),845.
2.    

orl-rat LD50:5000 mg/kg

    FCTXAV    Food and Cosmetics Toxicology. 17 (1979),845.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 2
RTECS: GY7301000

Specification

 Jasmone (CAS NO.488-10-8) is also named as (Z)-Jasmone ; 2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- ; 3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, (Z)- ; 3-Methyl-2-(cis-2-penten-1-yl)-2-cyclopenten-1-one ; 4-07-00-00337 (Beilstein Handbook Reference) ; BRN 1907713 ; FEMA No. 3196 . It is a colorless to pale yellow liquid that has the odor of jasmine. It slightly soluble in water, soluble in ethanol, ether and carbon tetrachloride and oil.