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4494-16-0

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4494-16-0 Usage

Uses

Octadec-9-enedioic Acid is a potential antioxidant and antimicrobial agent.

Check Digit Verification of cas no

The CAS Registry Mumber 4494-16-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,4,9 and 4 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 4494-16:
(6*4)+(5*4)+(4*9)+(3*4)+(2*1)+(1*6)=100
100 % 10 = 0
So 4494-16-0 is a valid CAS Registry Number.

4494-16-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Octadec-9-enedioic acid

1.2 Other means of identification

Product number -
Other names 9-octa-decenedioic acid

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:4494-16-0 SDS

4494-16-0Synthetic route

dec-9-enoic acid
14436-32-9

dec-9-enoic acid

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

Conditions
ConditionsYield
In toluene at 50℃; under 375.038 Torr; for 12h;91%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

A

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

B

9-octadecene
5557-31-3

9-octadecene

Conditions
ConditionsYield
With [1,3-bis(2,4,5-Me3Ph)-2-imidazolidinylidene]Ru=CHPh(PCy3)Cl2 at 45℃; for 24h;A 71%
B n/a
Stage #1: cis-Octadecenoic acid; dichloro(tricyclohexylphosphino)(benzylidene)(1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)ruthenium(III) at 45℃; for 24.08 - 72h; Neat (no solvent);
Stage #2: With ethyl vinyl ether Product distribution / selectivity;
A 71%
B n/a
Cl2(PCy3)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC6H5 at 20℃; for 96h; Product distribution / selectivity;A 21%
B 21%
With [1,3-bis(mesityl)-2-imidazolidinylidene]-[2-[[(2-methylphenyl)imino]-methyl]-phenolyl]-[3-phenyl-indenyliden]-ruthenium(II)chloride at 45℃; for 20h; Neat (no solvent);
Elaidic Acid
112-79-8

Elaidic Acid

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride at 50℃; for 24h; Inert atmosphere;64.5%

A

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

B

dodec-6-ene
29493-00-3

dodec-6-ene

C

pentadec-9-enoic acid
15451-50-0

pentadec-9-enoic acid

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride at 50℃; for 72h; Inert atmosphere;A 55.4%
B n/a
C n/a
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride at 45℃; for 72h; Inert atmosphere;47%
With D-sorbitol; water; urea; sodium hydroxide; yeast at 30℃; for 48h; pH=7 - 7.5; Enzymatic reaction;
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride at 45℃; for 24h; Inert atmosphere;29.75 g
With Hoveyda-Grubbs catalyst second generation; p-benzoquinone In n-heptane at 45℃; Inert atmosphere;
Ricinoleic acid
141-22-0

Ricinoleic acid

A

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

B

7,12-dihydroxyoctadec-9-ene
849663-74-7

7,12-dihydroxyoctadec-9-ene

Conditions
ConditionsYield
Stage #1: Ricinoleic acid; dichloro(tricyclohexylphosphino)(benzylidene)(1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)ruthenium(III) at 45 - 50℃; for 72h; Neat (no solvent);
Stage #2: With ethyl vinyl ether Product distribution / selectivity;
A n/a
B 40%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

ethene
74-85-1

ethene

A

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

B

1-Decene
872-05-9

1-Decene

C

dec-9-enoic acid
14436-32-9

dec-9-enoic acid

D

9-octadecene
5557-31-3

9-octadecene

Conditions
ConditionsYield
Cl2(PCy3)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC6H5 at 20℃; for 12h; Product distribution / selectivity;A 1%
B 37%
C 37%
D 1%
suberin

suberin

A

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

B

18-hydroxyoctadec-9-enoic acid
3329-38-2

18-hydroxyoctadec-9-enoic acid

C

C17H32O4

C17H32O4

D

9,16-dihydroxyhexadecanoic acid
38076-49-2, 69232-68-4

9,16-dihydroxyhexadecanoic acid

E

22-hydroxydocosanoic acid
506-45-6

22-hydroxydocosanoic acid

F

9,10,18-trihydroxyoctadecanoic acid
496-86-6

9,10,18-trihydroxyoctadecanoic acid

G

docosanedioic acid
505-56-6

docosanedioic acid

Conditions
ConditionsYield
Stage #1: suberin With sodium hydroxide In isopropyl alcohol for 1.25h; Heating / reflux;
Stage #2: With sulfuric acid In water at 100℃; pH=2 - 3;
1,4-butenediol
6117-80-2

1,4-butenediol

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

A

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

B

trans-2-undecen-1-ol
75039-83-7, 75039-84-8, 37617-03-1

trans-2-undecen-1-ol

C

ω-hydroxyundec-9-enoic acid
79868-94-3

ω-hydroxyundec-9-enoic acid

D

9-octadecene
5557-31-3

9-octadecene

Conditions
ConditionsYield
With C55H58ClN3ORu; Phenyltrichlorosilane In toluene at 50℃; for 5h;
cis-1,4-bis(acetyloxy)but-2-ene
25260-60-0

cis-1,4-bis(acetyloxy)but-2-ene

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

A

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

B

11-acetyloxy-9-undecenoic acid
101171-21-5

11-acetyloxy-9-undecenoic acid

C

undec-2-en-1-yl acetate
68480-27-3

undec-2-en-1-yl acetate

D

9-octadecene
5557-31-3

9-octadecene

Conditions
ConditionsYield
With C55H58ClN3ORu; Phenyltrichlorosilane In toluene at 50℃; for 5h;
cis-9-hexadecenoic acid
373-49-9

cis-9-hexadecenoic acid

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 6 h / 30 °C / 760.05 Torr
2: toluene / 12 h / 50 °C / 375.04 Torr
View Scheme
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

ethene
74-85-1

ethene

A

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

B

dec-9-enoic acid
14436-32-9

dec-9-enoic acid

Conditions
ConditionsYield
With [1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene][2-isopropoxy-5-(2,2,2-trifluoroacetamido)benzylidene]ruthenium(II) dichloride at 50℃; under 7500.75 Torr; for 2h; Autoclave;
dimethyl 9-octadecen-1,18-dioate
13481-97-5

dimethyl 9-octadecen-1,18-dioate

1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

Conditions
ConditionsYield
With water; sodium hydroxide at 80℃; for 1h;
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

9,10-dibromo-octadecanedioic acid
23550-15-4

9,10-dibromo-octadecanedioic acid

Conditions
ConditionsYield
With bromine In diethyl ether for 1h;83%
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

9,10-dihydroxyoctadecane-1,18-dioic acid
137-21-3

9,10-dihydroxyoctadecane-1,18-dioic acid

Conditions
ConditionsYield
Stage #1: 1,18-octadec-9-enedioic acid With potassium permanganate; potassium hydroxide In water at 0 - 50℃; for 0.216667h;
Stage #2: With hydrogenchloride; sodium thiosulfate; sodium sulfite In water
71%
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

acrylonitrile
107-13-1

acrylonitrile

10-cyano-9-decenoate
854401-56-2

10-cyano-9-decenoate

Conditions
ConditionsYield
bispyridine ruthenium complex In dichloromethane at 45℃; for 12h;50%
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With nonanoic acid; dihydrogen peroxide; ortho-tungstic acid at 78℃; for 24h;33%
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

methanol
67-56-1

methanol

dimethyl 9-octadecen-1,18-dioate
13481-97-5

dimethyl 9-octadecen-1,18-dioate

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 0.5h;
sulfuric acid at 80℃; for 0.5h; Product distribution / selectivity;
With sulfuric acid Inert atmosphere;
With sulfuric acid at 65℃; for 2h; Inert atmosphere;6.65 g
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

methanol
67-56-1

methanol

Ricinoleic acid
141-22-0

Ricinoleic acid

A

methyl ricinoleate
141-24-2

methyl ricinoleate

B

dimethyl 9-octadecen-1,18-dioate
13481-97-5

dimethyl 9-octadecen-1,18-dioate

Conditions
ConditionsYield
sulfuric acid Product distribution / selectivity;
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

A

methyl (Z)-10-cyano-9-decenoate
173602-45-4

methyl (Z)-10-cyano-9-decenoate

B

methyl (E)-10-cyano-9-decenoate
173602-43-2

methyl (E)-10-cyano-9-decenoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / Inert atmosphere
2: Hoveyda-Grubbs catalyst second generation / toluene / 16 h / 80 °C / Inert atmosphere
View Scheme
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

A

methyl 9-decenoate
25601-41-6

methyl 9-decenoate

B

methyl (E)-10-cyano-9-decenoate
173602-43-2

methyl (E)-10-cyano-9-decenoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / Inert atmosphere
2: Hoveyda-Grubbs catalyst second generation / toluene / 5 h / 100 °C / Inert atmosphere
View Scheme
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

8-cyano-octanoic acid
37056-34-1

8-cyano-octanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ammonia / zinc(II) oxide / 6 h / 300 °C / 760.05 Torr
2.1: ozone / pentane / 0.08 h / -70 - 0 °C
2.2: -70 °C
View Scheme
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

9-aminopelargonic methyl ester
4088-26-0

9-aminopelargonic methyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: ammonia / zinc(II) oxide / 6 h / 300 °C / 760.05 Torr
2.1: ozone / pentane / 0.08 h / -70 - 0 °C
2.2: -70 °C
3.1: sulfuric acid / benzene
4.1: ammonia / Raney nickel with 3 wtpercent of cobalt / ethanol / 4 h / 90 °C / 157516 Torr / Autoclave
View Scheme
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

methyl 10-cyano-2-decenoate
1226980-96-6

methyl 10-cyano-2-decenoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonia / zinc(II) oxide / 6 h / 300 °C / 760.05 Torr
2: Hoveyda-Grubbs catalyst second generation / 0.5 h / 50 °C / Inert atmosphere
View Scheme
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

8-cyanooctanoic acid methyl ester
38044-20-1

8-cyanooctanoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: ammonia / zinc(II) oxide / 6 h / 300 °C / 760.05 Torr
2.1: ozone / pentane / 0.08 h / -70 - 0 °C
2.2: -70 °C
3.1: sulfuric acid / benzene
View Scheme
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

C18H30N2
61549-45-9

C18H30N2

Conditions
ConditionsYield
With ammonia; zinc(II) oxide at 300℃; under 760.051 Torr; for 6h;86 %Chromat.
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

A

C26H50N2O4
1374264-74-0

C26H50N2O4

B

C26H50N2O4
1374264-73-9

C26H50N2O4

Conditions
ConditionsYield
at 145 - 180℃;
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

9-hydroxynonanoic acid
3788-56-5

9-hydroxynonanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydroxide; potassium permanganate / water / 0.22 h / 0 - 50 °C
2: sodium periodate; tetra(n-butyl)ammonium hydrogen sulfate / water; dichloromethane / 20 °C
3: sodium tetrahydroborate / 1,4-dioxane / 0 - 20 °C
View Scheme
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

azelaic acid semialdehyde
2553-17-5

azelaic acid semialdehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydroxide; potassium permanganate / water / 0.22 h / 0 - 50 °C
2: sodium periodate; tetra(n-butyl)ammonium hydrogen sulfate / water; dichloromethane / 20 °C
View Scheme
1,18-octadec-9-enedioic acid
4494-16-0

1,18-octadec-9-enedioic acid

18-((1,3-bis(oleoyloxy)propan-2-yl)oxy)-18-oxooctadec-9-enoic acid

18-((1,3-bis(oleoyloxy)propan-2-yl)oxy)-18-oxooctadec-9-enoic acid

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; Inert atmosphere;

4494-16-0Relevant articles and documents

Chain Multiplication of Fatty Acids to Precise Telechelic Polyethylene

Witt, Timo,H?u?ler, Manuel,Kulpa, Stefanie,Mecking, Stefan

supporting information, p. 7589 - 7594 (2017/06/13)

Starting from common monounsaturated fatty acids, a strategy is revealed that provides ultra-long aliphatic α,ω-difunctional building blocks by a sequence of two scalable catalytic steps that virtually double the chain length of the starting materials. The central double bond of the α,ω-dicarboxylic fatty acid self-metathesis products is shifted selectively to the statistically much-disfavored α,β-position in a catalytic dynamic isomerizing crystallization approach. “Chain doubling” by a subsequent catalytic olefin metathesis step, which overcomes the low reactivity of this substrates by using waste internal olefins as recyclable co-reagents, yields ultra-long-chain α,ω-difunctional building blocks of a precise chain length, as demonstrated up to a C48 chain. The unique nature of these structures is reflected by unrivaled melting points (Tm=120 °C) of aliphatic polyesters generated from these telechelic monomers, and by their self-assembly to polyethylene-like single crystals.

METHOD FOR SYNTHESISING BIOBASED UNSATURATED ACIDS

-

Paragraph 0071-0081, (2015/12/07)

The invention relates to a method for preparing a compound of formula (I), wherein n is an integer from 1 to 21,said method comprises reacting a light olefin fraction, in the presence of a metathesis catalyst, with a compound having from 10 to 24 carbon atoms, of the following formula (II): wherein, n is an integer from 1 to 21,R corresponds to a hydrogen atom or an alkyl or alkenyl chain from 1 to20 carbon atoms optionally substituted by at least one hydroxyl group, said compound of formula (II) being used alone or in a mixture of compounds of formula (II).

Synthesis of bio-based monomer from vegetable oil fatty acids and design of functionalized greener polyester

Abd. Rahim, Noor Farisha,Ariffin, Hidayah,Hassan, Mohd Ali,Watanabe, Kohtaro,Andou, Yoshito,Shirai, Yoshihito

supporting information, p. 1517 - 1519 (2014/12/11)

In order to design sustainable materials from vegetable oilbased fatty acids, we propose herewith a method to obtain unsaturated dicarboxylic acids as a polymerizable monomer through metathesis reaction of oleic and linoleic acids with the 2nd generation Grubbs catalyst. Subsequently, functional green polyester was produced from dicarboxylic acids and aromatic diol. Dicarboxylic acid having similar structure i.e., octadec-9-enedioic acid was successfully obtained from metathesis of both oleic and linoleic acids. Condensation polymerization of octadec-9-enedioic acid with 1,6-hexanediol and 4,4′-biphenol was carried out and it was shown that polymer with aromatic backbone had higher glass-transition temperature than aliphatic polyester.

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