Jasmone supplier | CasNO.488-10-8

Name
Jasmone
EINECS 207-668-4
CAS No. 488-10-8
Article Data97
CAS DataBase
Density 0.937 g/cm³
Solubility 1.48g/L at 20℃
Melting Point 203 - 205oC
Formula C₁₁H₁₆O
Boiling Point 264.2 °C at 760 mmHg
Molecular Weight 164.247
Flash Point 107.2 °C
Transport Information
Appearance COA
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
PSA 17.07000
LogP 3.02210

Synthetic route

: 7051-37-8
3-methyl-2-(2-pentynyl)-2-cyclopentenone

: 488-10-8
cis-jasmone

Conditions

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;

: 82909-46-4
3-bromo-2-<(Z)-2-pentenyl>-2-cyclopenten-1-one

lithium dimethylcuprate: lithium dimethylcuprate

: 488-10-8
cis-jasmone

Conditions

Conditions	Yield
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

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%

: 128192-01-8
2-(2-cis-pentenyl)-3-methyl-5-(phenylthio)-2-cyclopenten-1-one

: 488-10-8
cis-jasmone

Conditions

Conditions	Yield
With nickel In acetone	88%
With nickel

: 106763-43-3
methyl (Z)-2-<4-<(diethoxyphosphoryl)oxy>-1-oxo-4-pentenyl>-4-heptenoate

: 488-10-8
cis-jasmone

Conditions

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

: 32556-66-4, 32556-68-6, 87392-23-2, 131321-83-0, 135029-97-9, 135029-98-0
4-methyl-5-(2-pentenyl)cyclopent-2-en-1-one

: 488-10-8
cis-jasmone

Conditions

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

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

: 488-10-8
cis-jasmone

Conditions

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

: 488-10-8
cis-jasmone

Conditions

Conditions	Yield
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

Conditions	Yield
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

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;

: 165590-85-2
(Z)-3-methyl-2-(pent-2-enyl)cyclopent-2-enol

: 488-10-8
cis-jasmone

Conditions

Conditions	Yield
With jones reagent In acetone	62%

: 4868-21-7
undec-8c-ene-2,5-dione

A: 488-10-8
cis-jasmone

B: 6261-18-3
trans-jasmone

Conditions

Conditions	Yield
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

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

: 488-10-8
cis-jasmone

Conditions

Conditions	Yield
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

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;

: 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

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

...Expand

: 41031-88-3
(Z)-2-(2-pentenyl)-2-cyclopenten-1-one

: 917-54-4
methyllithium

: 488-10-8
cis-jasmone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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;

: 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

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

...Expand

(+-)-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

Conditions	Yield
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

Conditions	Yield
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

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

: 488-10-8
cis-jasmone

Conditions

Conditions	Yield
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

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%

: 488-10-8
cis-jasmone

: 1128-08-1
dihydro-cis-jasmone

Conditions

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%

: 488-10-8
cis-jasmone

: 64-19-7
acetic acid

: C13H18O3

Conditions

Conditions	Yield
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

Conditions	Yield
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

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%

: 488-10-8
cis-jasmone

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

Conditions

Conditions	Yield
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

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%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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%

: 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

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

...Expand

: 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

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

Jasmone Chemical Properties

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: C₁₁H₁₆O
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

Jasmone 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.

Jasmone Production

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

Jasmone 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.

Jasmone Consensus Reports

Reported in EPA TSCA Inventory.

Jasmone Safety Profile

Hazard Codes: Irritant Xi
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

Jasmone 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.

Product Name

Jasmone

Synthetic route

Jasmone Chemical Properties

Jasmone Uses

Jasmone Production

Jasmone Toxicity Data With Reference

Jasmone Consensus Reports

Jasmone Safety Profile

Jasmone Specification

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