Geranylacetone supplier | CasNO.689-67-8

Name
6,10-Dimethyl-5,9-undecadien-2-one
EINECS 211-711-2
CAS No. 689-67-8
Article Data52
CAS DataBase
Density 0.856 g/cm³
Solubility Not miscible or difficult to mix in water. Soluble in alcohol.
Melting Point
Formula C₁₃H₂₂O
Boiling Point 256.038 °C at 760 mmHg
Molecular Weight 194.317
Flash Point 107.443 °C
Transport Information
Appearance Colorless liquid or Light yellow liquid
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 5,9-Hendecadien-2-one,6,10-dimethyl- (4CI);2,6-Dimethylundeca-2,6-dien-10-one;6,10-Dimethyl-5,9-undec-2-one;6,10-Dimethyl-5,9-undecadien-2-one;6,10-Dimethyl-5,9-undecadiene-2-one;Dihydropseudoionone;NSC 406679;
PSA 17.07000
LogP 4.04830

Synthetic route

: 141-10-6
pseudoionone

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With phenylsilane; C3H7CuF*FH In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; chemoselective reaction;	96%
With ethanol; nickel Hydrogenation;
With nickel at 50℃; Hydrogenation;

: 25456-03-5
3,7-Dimethylocta-1,6-dien-3-yl acetoacetate

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With aluminum oxide at 60℃; for 3h;	95%
With aluminum oxide at 60℃; for 5h; other allyl acetoacetates;	75%
With aluminum oxide at 60℃; for 5h;	75%
With palladium diacetate; triphenylphosphine In tert-butyl alcohol at 50℃; for 2h;	56%
at 170 - 235℃;

: 78-70-6
3,7-dimethylocta-1,6-dien-3-ol

: 116-11-0
2-Methoxypropene

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
ammonium chloride at 140℃; for 40h; Product distribution / selectivity; Autoclave;	93.1%
With phenylphosphinic acid

: 134451-02-8
3-chloro-6,10-dimethyl-undeca-5,9-dien-2-one

: 87887-37-4
3-Chloro-10-methyl-6-methylene-undec-9-en-2-one

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine; lithium chloride In various solvent(s) at 150℃; for 2.5h;	88%

: 78-70-6
3,7-dimethylocta-1,6-dien-3-ol

: 105-45-3
acetoacetic acid methyl ester

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With aluminum oxide In methanol at 170℃; for 5.5h; Temperature;	85.68%

: 418768-53-3
C15H24O2

A: 689-67-8
pseudo-ionone

B: 129970-89-4
C14H24O

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-benzene at 140℃; for 14h; Sealed tube; Inert atmosphere;	A 30% B 64%

: 108-24-7
acetic anhydride

: C11H19IMg

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
In diethyl ether at -72℃;	44.7%

: 50373-44-9
C13H24O

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With dichloro(benzene)ruthenium(II) dimer; mono(3-deoxy-3-[N-(2-hydroxyethyl)amino])-β-cyclodextrin; sodium formate In water; N,N-dimethyl-formamide at 50℃; for 12h; optical yield given as %ee; enantioselective reaction;	35%

: 19317-11-4
farnesal

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With potassium carbonate

: 111-02-4
squalene

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With potassium permanganate; acetone bei gewoehnlicher Temperatur;

: 10032-00-5
acetoacetic acid-(3,7-dimethyl-octa-2,6-dienyl ester)

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
at 220 - 230℃;

: 4490-10-2
geranyl chloride

: 141-97-9
ethyl acetoacetate

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With potassium carbonate; acetone

: 126-91-0
linalool

: 141-52-6
sodium ethanolate

: 141-97-9
ethyl acetoacetate

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
at 200 - 220℃; analoge Umsetzung mit 2-Butyl-acetessigester;

...Expand

: 78-70-6
3,7-dimethylocta-1,6-dien-3-ol

: 141-97-9
ethyl acetoacetate

: 689-67-8
pseudo-ionone

: 106-24-1
Geraniol

: 141-97-9
ethyl acetoacetate

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With ethanol; sodium ethanolate at 200℃;
With ethanol; sodium acetate at 200℃;

: 141-10-6
pseudoionone

A: 1604-34-8
6,10-dimethyl-undecan-2-one

B: 689-67-8
pseudo-ionone

C: 4433-36-7
6,10-dimethyl-9-undecen-2-one

Conditions

Conditions	Yield
With hydrogen; nickel In isopropyl alcohol at 20℃; under 60754.8 Torr; for 0.0833333h; Rate constant; other temperatures;

...Expand

: 6138-90-5
geranyl bromide

: 141-97-9
ethyl acetoacetate

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With sodium In ethanol

: 85217-73-8
(Z)-3,7-dimethylocta-2,6-dien-1-yl methyl carbonate

: 105-45-3
acetoacetic acid methyl ester

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With sodium hydroxide; oxonium; 1,2-bis-(diphenylphosphino)ethane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex 1.) THF, 50 deg C, 3 h; Yield given. Multistep reaction;

: 85217-72-7
geranyl methyl carbonate

: 105-45-3
acetoacetic acid methyl ester

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With sodium hydroxide; oxonium; 1,2-bis-(diphenylphosphino)ethane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex 1.) THF, 50 deg C, 3 h; Yield given. Multistep reaction;

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 105-45-3
acetoacetic acid methyl ester

: 107-18-6
allyl alcohol

A: 689-67-8
pseudo-ionone

B: 141-10-6
pseudoionone

C: 134143-47-8
(E)-10-Methyl-6-methylene-undeca-3,9-dien-2-one

D: 105737-79-9
10-methyl-6-methylene-undec-9-en-2-one

Conditions

Conditions	Yield
Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

...Expand

: 64-17-5
ethanol

: 106-24-1
Geraniol

: 141-52-6
sodium ethanolate

: 141-97-9
ethyl acetoacetate

A: 689-67-8
pseudo-ionone

B geranyl acetate: geranyl acetate

Conditions

Conditions	Yield
at 200℃;

...Expand

: 64-17-5
ethanol

: 106-24-1
Geraniol

: 127-09-3
sodium acetate

: 141-97-9
ethyl acetoacetate

A: 689-67-8
pseudo-ionone

B geranyl acetate: geranyl acetate

Conditions

Conditions	Yield
at 200℃;

...Expand

2-geranyl-acetoacetic acid ester: 2-geranyl-acetoacetic acid ester

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With barium dihydroxide

: 77532-61-7
acetyl-2 dimethyl-5,9 decadiene-4,8 oate d'ethyle

aq. barium hydroxide solution: aq. barium hydroxide solution

: 689-67-8
pseudo-ionone

farnesenic acid nitrile: farnesenic acid nitrile

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With sodium hydroxide

geranylacetoacetic acid ester: geranylacetoacetic acid ester

: 689-67-8
pseudo-ionone

Conditions

Conditions	Yield
With alkali

: 64-17-5
ethanol

: 77532-61-7
acetyl-2 dimethyl-5,9 decadiene-4,8 oate d'ethyle

KOH-solution: KOH-solution

: 689-67-8
pseudo-ionone

...Expand

: 111-02-4
squalene

: 67-64-1
acetone

permanganate: permanganate

A: 110-93-0
6-Methyl-hept-5-en-2-on

B: 110-15-6
succinic acid

C: 689-67-8
pseudo-ionone

...Expand

: 872275-34-8
8,12-dimethyl-trideca-2,7,11-trien-4-one

aqueous K2CO3: aqueous K2CO3

A: 689-67-8
pseudo-ionone

B: 75-07-0
acetaldehyde

...Expand

: 689-67-8
pseudo-ionone

: 29681-57-0
tert-butyldimethylsilane

: tert-butyl-dimethyl-(1,5,9-trimethyl-deca-4,8-dienyloxy)-silane

Conditions

Conditions	Yield
With (S)-DM-SEGPHOS; sodium methylate; copper(l) chloride In diethyl ether at 20℃;	99%

: 689-67-8
pseudo-ionone

: 106-95-6
allyl bromide

: C16H28O

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine; chloro-trimethyl-silane; bis(cyclopentadienyl)titanium (III) chloride In tetrahydrofuran at 20℃; for 6h; Barbier type allylation; Inert atmosphere;	98%

: 689-67-8
pseudo-ionone

: 107-21-1
ethylene glycol

: 69538-03-0
2-(4,8-dimethylnona-3,7-dienyl)-2-methyl-1,3-dioxolane

Conditions

Conditions	Yield
With Amberlyst 15 In benzene at 20 - 100℃; for 12h; Inert atmosphere; Dean-Stark;	97%

: 689-67-8
pseudo-ionone

: 193481-15-1
4-bromo-2-(triisopropylsilyloxy)furan

: 4-(1-hydroxy-1,5,9-trimethyl-deca-4,8-dienyl)-5H-furan-2-one

Conditions

Conditions	Yield
Stage #1: 4-bromo-2-(triisopropylsilyloxy)furan With n-butyllithium In tetrahydrofuran; hexane at -78 - -40℃; for 0.583333h; Metallation; Stage #2: pseudo-ionone In tetrahydrofuran; hexane at -78℃; Addition;	94%

: 689-67-8
pseudo-ionone

: 103583-50-2, 103583-59-1
(E)-6-Methyl-undec-5-en-9-yn-2-one

Conditions

Conditions	Yield
With sodium nitrite In water; acetic acid 1.) 0 deg C 2.) 60 deg C, 0.5 h;	91%

: 689-67-8
pseudo-ionone

: 74-86-2
acetylene

: 2387-68-0, 54325-12-1
3,7,11-trimethyl-6,10-dodecadien-1-yn-3-ol

Conditions

Conditions	Yield
	90%

: 689-67-8
pseudo-ionone

: 624-65-7
2-propynyl chloride

: 57419-22-4
4,8,12-trimethyl-trideca-7,11-dien-1-yn-4-ol

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 7h; Barbier Coupling Reaction; Inert atmosphere; chemoselective reaction;	89%
With manganese; TiCpCl2 In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;	77%

: 689-67-8
pseudo-ionone

: 4301-14-8
acetylenemagnesium bromide

: 2387-68-0, 54325-12-1
3,7,11-trimethyl-6,10-dodecadien-1-yn-3-ol

Conditions

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; for 1h;	88%
In tetrahydrofuran at 0℃; for 0.5h;	87%

: 689-67-8
pseudo-ionone

: 107-05-1
3-chloroprop-1-ene

: C16H28O

Conditions

Conditions	Yield
With manganese; TiCpCl2 In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	85%

: 56-23-5
tetrachloromethane

: 689-67-8
pseudo-ionone

: 1,1-dichloro-2,6,10-trimethylundec-1,5,9-triene

Conditions

Conditions	Yield
With titanocene(II) triethylphosphite complex In tetrahydrofuran at 0℃; for 2h;	72%

: 689-67-8
pseudo-ionone

: 121725-70-0
but-2-enyl ethyl carbonate

: 1293996-63-0
C17H30O

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; tertiary butyl chloride; triphenylphosphine; palladium dichloride In tetrahydrofuran at 20℃; for 16h; Barbier reaction; Inert atmosphere; regioselective reaction;	71%

: 689-67-8
pseudo-ionone

: 145100-51-2
N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

: C14H21F3O3S

Conditions

Conditions	Yield
With potassium hexamethylsilazane In tetrahydrofuran at -78℃;	61%

: 689-67-8
pseudo-ionone

: 5927-18-4
trimethyl phosphonoacetate

: 10485-70-8
methyl 3,7,11-trimethyldodeca-2,6,10-trienoate

Conditions

Conditions	Yield
With sodium methylate In methanol for 20h; Ambient temperature;	59%

: 689-67-8
pseudo-ionone

: 927-80-0
1-ethoxyacetylene

: 20723-88-0
ethyl 3,7,11-trimethyldodeca-2,6,10-trienoate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether for 0.5h;	48%

: 689-67-8
pseudo-ionone

: 96-34-4
methyl chloroacetate

: 25427-23-0
methyl 3-(4,8-dimethylnona-3,7-dienyl)-3-methyloxirane-2-carboxylate

Conditions

Conditions	Yield
Stage #1: pseudo-ionone With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol for 0.25h; Stage #2: methyl chloroacetate In tetrahydrofuran; tert-butyl alcohol for 12h;	35%

: 689-67-8
pseudo-ionone

: 160096-44-6
α-ionone

Conditions

Conditions	Yield
With zeolite CaY at 105℃; for 6h;	23%

: 110-52-1
1,4-dibromo-butane

: 689-67-8
pseudo-ionone

: 111-02-4
squalene

Conditions

Conditions	Yield
With diethyl ether; iodine; magnesium at 100℃;

: 50-00-0
formaldehyd

: 689-67-8
pseudo-ionone

: 104121-85-9
3-hydroxymethyl-6,10-dimethyl-undeca-5,9-dien-2-one

Conditions

Conditions	Yield
With barium dihydroxide at 60℃; spaeter auf 100grad;

: 689-67-8
pseudo-ionone

: 925-90-6
ethylmagnesium bromide

: 3625-49-8
3,7,11-trimethyl-6,10-dodecadien-3-ol

Conditions

Conditions	Yield
With diethyl ether

: 689-67-8
pseudo-ionone

: 925-90-6
ethylmagnesium bromide

A: 20663-13-2
(Z)-3,7,11-trimethyl-dodeca-6,10-dien-3-ol

B: 20685-70-5
(+/-)-3,7,11-trimethyl-dodeca-6t,10-dien-3-ol

Conditions

Conditions	Yield
With diethyl ether

...Expand

Geranylacetone Chemical Properties

CAS: 689-67-8
MF: C₁₃H₂₂O
MW: 194.31
EINECS: 223-269-8
Product Categories: Acyclic Monoterpenes;Biochemistry;Terpenes
Mol File: 689-67-8.mol
bp： 254-258 °C(lit.)
density： 0.873 g/mL at 25 °C(lit.)
FEMA： 3542
refractive index： n20/D 1.467(lit.)
Fp： >230 °F
Synonyms:9-Undecadien-2-one,6,10-dimethyl-5;alpha,beta-Dihydropseudoionone;Dihydropseudoionone;TRANS-6,10-DIMETHYL-5,9-UNDECADIEN-2-ONE;GERANYL-2-PROPANONE;FEMA 3542;CBI-BB ZERO/001230;6,10-DIMETHYLUNDECA-5,9-DIEN-2-ONE
The structure of GERANYL ACETONE is:

Geranylacetone Toxicity Data With Reference

skn-rbt 500 mg/24H MOD

FCTXAV Food and Cosmetics Toxicology. 17 (1979),787.

Geranylacetone Consensus Reports

GERANYL ACETONE is reported in EPA TSCA Inventory.

Geranylacetone Safety Profile

Hazard Codes： Xi
Risk Statements： 36/37/38
Safety Statements： 26-37/39
WGK Germany： 3
RTECS： YQ1190000
A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Product Name

6,10-Dimethyl-5,9-undecadien-2-one

Synthetic route

Geranylacetone Chemical Properties

Geranylacetone Toxicity Data With Reference

Geranylacetone Consensus Reports

Geranylacetone Safety Profile

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