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689-67-8 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 689-67-8 differently. You can refer to the following data:
1. Geranylacetone occurs in (5Z)-trans as well as in (5E)-trans form and has been identified in fruits and in essential oils. It is a colorless liquid with a fresh, green, slightly penetrating, rose-like odor. Geranylacetone is an intermediate in the synthesis of other fragrance substances. It is mainly produced from linalool. Another route starts from myrcene, to which methyl acetoacetate is added under rhodium catalysis; geranylacetone is subsequently obtained after saponification and decarboxylation. It is used in perfumery in rose compositions, for example, in soap perfumes.
2. 6,10-Dimethyl-5,9-undecadien-2-one has a green and rosy floral odor and fresh-floral, light, but rather penetrating sweet-rosy, slightly green, magnolia-like odor. It blends well in lavender and fruity notes, where it imparts a clean and natural character. It helps to round out floral bouquets

Uses

It is used as a flavoring agent and adjuvant. It is also employed as a substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.

Application

Geranylacetone is an intermediate in nerolidol synthesis. It is used in perfumery in rose compositions, for example, in soap perfumes.

General Description

6,10-Dimethyl-5,9-undecadien-2-one is one of the key volatile flavor compounds of tomato and certain species of mushroom.

Safety Profile

A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 689-67-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,8 and 9 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 689-67:
(5*6)+(4*8)+(3*9)+(2*6)+(1*7)=108
108 % 10 = 8
So 689-67-8 is a valid CAS Registry Number.
InChI:InChI=1/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9+

689-67-8 Well-known Company Product Price

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  • TCI America

  • (G0236)  Geranylacetone [mixture of (E)- and (Z)- isomers, (3:2)]  >96.0%(GC)

  • 689-67-8

  • 25mL

  • 420.00CNY

  • Detail

689-67-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Geranylacetone

1.2 Other means of identification

Product number -
Other names 6,10-Dimethyl-5,9-undecadien-2-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:689-67-8 SDS

689-67-8Synthetic route

pseudoionone
141-10-6

pseudoionone

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
With phenylsilane; C3H7CuF*FH In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; chemoselective reaction;96%
With ethanol; nickel Hydrogenation;
With nickel at 50℃; Hydrogenation;
3,7-Dimethylocta-1,6-dien-3-yl acetoacetate
25456-03-5

3,7-Dimethylocta-1,6-dien-3-yl acetoacetate

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
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℃;
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

2-Methoxypropene
116-11-0

2-Methoxypropene

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
ammonium chloride at 140℃; for 40h; Product distribution / selectivity; Autoclave;93.1%
With phenylphosphinic acid
3-chloro-6,10-dimethyl-undeca-5,9-dien-2-one
134451-02-8

3-chloro-6,10-dimethyl-undeca-5,9-dien-2-one

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

3-Chloro-10-methyl-6-methylene-undec-9-en-2-one

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; lithium chloride In various solvent(s) at 150℃; for 2.5h;88%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
With aluminum oxide In methanol at 170℃; for 5.5h; Temperature;85.68%
C15H24O2
418768-53-3

C15H24O2

A

pseudo-ionone
689-67-8

pseudo-ionone

B

C14H24O
129970-89-4

C14H24O

Conditions
ConditionsYield
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%
acetic anhydride
108-24-7

acetic anhydride

C11H19IMg

C11H19IMg

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
In diethyl ether at -72℃;44.7%
C13H24O
50373-44-9

C13H24O

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
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%
farnesal
19317-11-4

farnesal

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
With potassium carbonate
squalene
111-02-4

squalene

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
With potassium permanganate; acetone bei gewoehnlicher Temperatur;
acetoacetic acid-(3,7-dimethyl-octa-2,6-dienyl ester)
10032-00-5

acetoacetic acid-(3,7-dimethyl-octa-2,6-dienyl ester)

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
at 220 - 230℃;
geranyl chloride
4490-10-2

geranyl chloride

ethyl acetoacetate
141-97-9

ethyl acetoacetate

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
With potassium carbonate; acetone
linalool
126-91-0

linalool

sodium ethanolate
141-52-6

sodium ethanolate

ethyl acetoacetate
141-97-9

ethyl acetoacetate

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
at 200 - 220℃; analoge Umsetzung mit 2-Butyl-acetessigester;
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

ethyl acetoacetate
141-97-9

ethyl acetoacetate

pseudo-ionone
689-67-8

pseudo-ionone

Geraniol
106-24-1

Geraniol

ethyl acetoacetate
141-97-9

ethyl acetoacetate

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
With ethanol; sodium ethanolate at 200℃;
With ethanol; sodium acetate at 200℃;
pseudoionone
141-10-6

pseudoionone

A

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

6,10-dimethyl-undecan-2-one

B

pseudo-ionone
689-67-8

pseudo-ionone

C

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

6,10-dimethyl-9-undecen-2-one

Conditions
ConditionsYield
With hydrogen; nickel In isopropyl alcohol at 20℃; under 60754.8 Torr; for 0.0833333h; Rate constant; other temperatures;
geranyl bromide
6138-90-5

geranyl bromide

ethyl acetoacetate
141-97-9

ethyl acetoacetate

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
With sodium In ethanol
(Z)-3,7-dimethylocta-2,6-dien-1-yl methyl carbonate
85217-73-8

(Z)-3,7-dimethylocta-2,6-dien-1-yl methyl carbonate

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
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;
geranyl methyl carbonate
85217-72-7

geranyl methyl carbonate

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
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;
7-methyl-3-methene-1,6-octadiene
123-35-3

7-methyl-3-methene-1,6-octadiene

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

allyl alcohol
107-18-6

allyl alcohol

A

pseudo-ionone
689-67-8

pseudo-ionone

B

pseudoionone
141-10-6

pseudoionone

C

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

(E)-10-Methyl-6-methylene-undeca-3,9-dien-2-one

D

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

10-methyl-6-methylene-undec-9-en-2-one

Conditions
ConditionsYield
Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;
ethanol
64-17-5

ethanol

Geraniol
106-24-1

Geraniol

sodium ethanolate
141-52-6

sodium ethanolate

ethyl acetoacetate
141-97-9

ethyl acetoacetate

A

pseudo-ionone
689-67-8

pseudo-ionone

B

geranyl acetate

geranyl acetate

Conditions
ConditionsYield
at 200℃;
ethanol
64-17-5

ethanol

Geraniol
106-24-1

Geraniol

sodium acetate
127-09-3

sodium acetate

ethyl acetoacetate
141-97-9

ethyl acetoacetate

A

pseudo-ionone
689-67-8

pseudo-ionone

B

geranyl acetate

geranyl acetate

Conditions
ConditionsYield
at 200℃;
2-geranyl-acetoacetic acid ester

2-geranyl-acetoacetic acid ester

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
With barium dihydroxide
acetyl-2 dimethyl-5,9 decadiene-4,8 oate d'ethyle
77532-61-7

acetyl-2 dimethyl-5,9 decadiene-4,8 oate d'ethyle

aq. barium hydroxide solution

aq. barium hydroxide solution

pseudo-ionone
689-67-8

pseudo-ionone

farnesenic acid nitrile

farnesenic acid nitrile

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
With sodium hydroxide
geranylacetoacetic acid ester

geranylacetoacetic acid ester

pseudo-ionone
689-67-8

pseudo-ionone

Conditions
ConditionsYield
With alkali
ethanol
64-17-5

ethanol

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

acetyl-2 dimethyl-5,9 decadiene-4,8 oate d'ethyle

KOH-solution

KOH-solution

pseudo-ionone
689-67-8

pseudo-ionone

squalene
111-02-4

squalene

acetone
67-64-1

acetone

permanganate

permanganate

A

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

6-Methyl-hept-5-en-2-on

B

succinic acid
110-15-6

succinic acid

C

pseudo-ionone
689-67-8

pseudo-ionone

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

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

aqueous K2CO3

aqueous K2CO3

A

pseudo-ionone
689-67-8

pseudo-ionone

B

acetaldehyde
75-07-0

acetaldehyde

pseudo-ionone
689-67-8

pseudo-ionone

tert-butyldimethylsilane
29681-57-0

tert-butyldimethylsilane

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

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

Conditions
ConditionsYield
With (S)-DM-SEGPHOS; sodium methylate; copper(l) chloride In diethyl ether at 20℃;99%
pseudo-ionone
689-67-8

pseudo-ionone

allyl bromide
106-95-6

allyl bromide

C16H28O

C16H28O

Conditions
ConditionsYield
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%
pseudo-ionone
689-67-8

pseudo-ionone

ethylene glycol
107-21-1

ethylene glycol

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

2-(4,8-dimethylnona-3,7-dienyl)-2-methyl-1,3-dioxolane

Conditions
ConditionsYield
With Amberlyst 15 In benzene at 20 - 100℃; for 12h; Inert atmosphere; Dean-Stark;97%
pseudo-ionone
689-67-8

pseudo-ionone

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

4-bromo-2-(triisopropylsilyloxy)furan

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

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

Conditions
ConditionsYield
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%
pseudo-ionone
689-67-8

pseudo-ionone

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

(E)-6-Methyl-undec-5-en-9-yn-2-one

Conditions
ConditionsYield
With sodium nitrite In water; acetic acid 1.) 0 deg C 2.) 60 deg C, 0.5 h;91%
pseudo-ionone
689-67-8

pseudo-ionone

acetylene
74-86-2

acetylene

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

3,7,11-trimethyl-6,10-dodecadien-1-yn-3-ol

Conditions
ConditionsYield
90%
pseudo-ionone
689-67-8

pseudo-ionone

2-propynyl chloride
624-65-7

2-propynyl chloride

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

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

Conditions
ConditionsYield
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%
pseudo-ionone
689-67-8

pseudo-ionone

acetylenemagnesium bromide
4301-14-8

acetylenemagnesium bromide

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

3,7,11-trimethyl-6,10-dodecadien-1-yn-3-ol

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃; for 1h;88%
In tetrahydrofuran at 0℃; for 0.5h;87%
pseudo-ionone
689-67-8

pseudo-ionone

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

3-chloroprop-1-ene

C16H28O

C16H28O

Conditions
ConditionsYield
With manganese; TiCpCl2 In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;85%
tetrachloromethane
56-23-5

tetrachloromethane

pseudo-ionone
689-67-8

pseudo-ionone

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

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

Conditions
ConditionsYield
With titanocene(II) triethylphosphite complex In tetrahydrofuran at 0℃; for 2h;72%
pseudo-ionone
689-67-8

pseudo-ionone

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

but-2-enyl ethyl carbonate

C17H30O
1293996-63-0

C17H30O

Conditions
ConditionsYield
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%
pseudo-ionone
689-67-8

pseudo-ionone

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

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

C14H21F3O3S

C14H21F3O3S

Conditions
ConditionsYield
With potassium hexamethylsilazane In tetrahydrofuran at -78℃;61%
pseudo-ionone
689-67-8

pseudo-ionone

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

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

methyl 3,7,11-trimethyldodeca-2,6,10-trienoate

Conditions
ConditionsYield
With sodium methylate In methanol for 20h; Ambient temperature;59%
pseudo-ionone
689-67-8

pseudo-ionone

1-ethoxyacetylene
927-80-0

1-ethoxyacetylene

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

ethyl 3,7,11-trimethyldodeca-2,6,10-trienoate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In diethyl ether for 0.5h;48%
pseudo-ionone
689-67-8

pseudo-ionone

methyl chloroacetate
96-34-4

methyl chloroacetate

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

methyl 3-(4,8-dimethylnona-3,7-dienyl)-3-methyloxirane-2-carboxylate

Conditions
ConditionsYield
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%
pseudo-ionone
689-67-8

pseudo-ionone

α-ionone
160096-44-6

α-ionone

Conditions
ConditionsYield
With zeolite CaY at 105℃; for 6h;23%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

pseudo-ionone
689-67-8

pseudo-ionone

squalene
111-02-4

squalene

Conditions
ConditionsYield
With diethyl ether; iodine; magnesium at 100℃;
formaldehyd
50-00-0

formaldehyd

pseudo-ionone
689-67-8

pseudo-ionone

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

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

Conditions
ConditionsYield
With barium dihydroxide at 60℃; spaeter auf 100grad;
pseudo-ionone
689-67-8

pseudo-ionone

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

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

3,7,11-trimethyl-6,10-dodecadien-3-ol

Conditions
ConditionsYield
With diethyl ether
pseudo-ionone
689-67-8

pseudo-ionone

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

A

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

(Z)-3,7,11-trimethyl-dodeca-6,10-dien-3-ol

B

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

(+/-)-3,7,11-trimethyl-dodeca-6t,10-dien-3-ol

Conditions
ConditionsYield
With diethyl ether

689-67-8Relevant articles and documents

Litvak,M.M. et al.

, (1979)

Capturing the Monomeric (L)CuH in NHC-Capped Cyclodextrin: Cavity-Controlled Chemoselective Hydrosilylation of α,β-Unsaturated Ketones

Bistri-Aslanoff, Olivia,Derat, Etienne,Leloux, Sébastien,Leyssens, Tom,Ménand, Micka?l,Meijide Suárez, Jorge,Riant, Olivier,Roland, Sylvain,Sollogoub, Matthieu,Xu, Guangcan,Zhang, Pinglu,Zhang, Yongmin

supporting information, p. 7591 - 7597 (2020/03/23)

The encapsulation of copper inside a cyclodextrin capped with an N-heterocyclic carbene (ICyD) allowed both to catch the elusive monomeric (L)CuH and a cavity-controlled chemoselective copper-catalyzed hydrosilylation of α,β-unsaturated ketones. Remarkably, (α-ICyD)CuCl promoted the 1,2-addition exclusively, while (β-ICyD)CuCl produced the fully reduced product. The chemoselectivity is controlled by the size of the cavity and weak interactions between the substrate and internal C?H bonds of the cyclodextrin.

A ruthenium complex compound for the selective hydrogenation of the dienone method

-

Paragraph 0050-0052, (2019/07/04)

The invention provides a selective hydrogenation of ruthenium complex α, γ - unsaturated dienone method, and in particular relates to a method for using the hydrogen in the catalyst under the action of the α, γ - unsaturated dienone is reduced to the corresponding γ - unsaturated ketone of the method, the catalyst employed for ruthenium complex, a ruthenium precursor and the ligand in-situ prepared. Major advantage of this invention is characterized in that the catalyst is composed of metal precursor and the ligand in-situ prepared, simple operation, high catalyst activity; pyridine, quinoline nitrogen-containing aromatic heterocycle such as the adding of the poisoned medicinal preparation, effectively restraining the product γ - unsaturated ketone transition hydrogenation reaction, an excellent selectivity, the cost is low.

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