9-Octadecenedioic acid supplier

Name
8-Hexadecene-1,16-dicarboxylic acid
EINECS
CAS No. 4494-16-0
Article Data14
CAS DataBase
Density 1.012g/cm³
Solubility
Melting Point 102.5-103.5℃ (ethyl acetate )
Formula C₁₈H₃₂O₄
Boiling Point 426.4 °C at 760 mmHg
Molecular Weight 312.45
Flash Point 225.8 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,18-Octadec-9-enedioicacid;Hexadec-8-ene-1,16-dicarboxylic acid;Homocivetic acid;Octadec-9-ene-1,18-dioic acid;
PSA 74.60000
LogP 5.17320

Synthetic route

: 14436-32-9
dec-9-enoic acid

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

Conditions

Conditions	Yield
In toluene at 50℃; under 375.038 Torr; for 12h;	91%

: 112-80-1
cis-Octadecenoic acid

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

B: 5557-31-3
9-octadecene

Conditions

Conditions	Yield
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);

: 112-79-8
Elaidic Acid

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

Conditions

Conditions	Yield
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%

: 60-33-3, 506-21-8, 2197-37-7, 2420-42-0, 2420-55-5
9,12-octadecadienoic acid

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

B: 29493-00-3
dodec-6-ene

C: 15451-50-0
pentadec-9-enoic acid

Conditions

Conditions	Yield
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

...Expand

: 112-80-1
cis-Octadecenoic acid

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

Conditions

Conditions	Yield
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;

: 141-22-0
Ricinoleic acid

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

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

Conditions

Conditions	Yield
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%

: 112-80-1
cis-Octadecenoic acid

: 74-85-1
ethene

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

B: 872-05-9
1-Decene

C: 14436-32-9
dec-9-enoic acid

D: 5557-31-3
9-octadecene

Conditions

Conditions	Yield
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%

...Expand

suberin: suberin

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

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

C: C17H32O4

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

E: 506-45-6
22-hydroxydocosanoic acid

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

G: 505-56-6
docosanedioic acid

Conditions

Conditions	Yield
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;

...Expand

: 6117-80-2
1,4-butenediol

: 112-80-1
cis-Octadecenoic acid

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

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

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

D: 5557-31-3
9-octadecene

Conditions

Conditions	Yield
With C55H58ClN3ORu; Phenyltrichlorosilane In toluene at 50℃; for 5h;

...Expand

: 25260-60-0
cis-1,4-bis(acetyloxy)but-2-ene

: 112-80-1
cis-Octadecenoic acid

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

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

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

D: 5557-31-3
9-octadecene

Conditions

Conditions	Yield
With C55H58ClN3ORu; Phenyltrichlorosilane In toluene at 50℃; for 5h;

...Expand

: 373-49-9
cis-9-hexadecenoic acid

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

Conditions

Conditions	Yield
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

: 112-80-1
cis-Octadecenoic acid

: 74-85-1
ethene

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

B: 14436-32-9
dec-9-enoic acid

Conditions

Conditions	Yield
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;

...Expand

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

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

Conditions

Conditions	Yield
With water; sodium hydroxide at 80℃; for 1h;

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

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

Conditions

Conditions	Yield
With bromine In diethyl ether for 1h;	83%

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

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

Conditions

Conditions	Yield
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%

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

: 107-13-1
acrylonitrile

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

Conditions

Conditions	Yield
bispyridine ruthenium complex In dichloromethane at 45℃; for 12h;	50%

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

: 123-99-9
azelaic acid

Conditions

Conditions	Yield
With nonanoic acid; dihydrogen peroxide; ortho-tungstic acid at 78℃; for 24h;	33%

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

: 67-56-1
methanol

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

Conditions

Conditions	Yield
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

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

: 67-56-1
methanol

: 141-22-0
Ricinoleic acid

A: 141-24-2
methyl ricinoleate

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

Conditions

Conditions	Yield
sulfuric acid Product distribution / selectivity;

...Expand

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

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

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

Conditions

Conditions	Yield
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

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

A: 25601-41-6
methyl 9-decenoate

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

Conditions

Conditions	Yield
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

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

: 37056-34-1
8-cyano-octanoic acid

Conditions

Conditions	Yield
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

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

: 4088-26-0
9-aminopelargonic methyl ester

Conditions

Conditions	Yield
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

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

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

Conditions

Conditions	Yield
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

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

: 38044-20-1
8-cyanooctanoic acid methyl ester

Conditions

Conditions	Yield
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

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

: 61549-45-9
C18H30N2

Conditions

Conditions	Yield
With ammonia; zinc(II) oxide at 300℃; under 760.051 Torr; for 6h;	86 %Chromat.

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

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

A: 1374264-74-0
C26H50N2O4

B: 1374264-73-9
C26H50N2O4

Conditions

Conditions	Yield
at 145 - 180℃;

...Expand

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

: 3788-56-5
9-hydroxynonanoic acid

Conditions

Conditions	Yield
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

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

: 2553-17-5
azelaic acid semialdehyde

Conditions

Conditions	Yield
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

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

: 2465-32-9, 98168-52-6
1,3-diolein

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

Conditions

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

9-Octadecenedioic acid Specification

The 9-Octadecenedioic acid, with CAS registry number 4494-16-0, has the systematic name of octadec-9-enedioic acid. Besides this, it is also called 8-Hexadecene-1,16-dicarboxylic acid. And the chemical formula of this chemical is C₁₈H₃₂O₄.

Physical properties of 9-Octadecenedioic acid: (1)ACD/LogP: 5.59; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 4; (4)ACD/LogD (pH 7.4): 0.98; (5)#H bond acceptors: 4; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 16; (8)Polar Surface Area: 74.6 Å²; (9)Index of Refraction: 1.486; (10)Molar Refractivity: 88.62 cm³; (11)Molar Volume: 308.5 cm³; (12)Polarizability: 35.13×10^-24cm³; (13)Surface Tension: 40.6 dyne/cm; (14)Density: 1.012 g/cm³; (15)Flash Point: 225.8 °C; (16)Enthalpy of Vaporization: 74.71 kJ/mol; (17)Boiling Point: 426.4 °C at 760 mmHg; (18)Vapour Pressure: 1.82E-08 mmHg at 25°C.

Preparation: this chemical can be prepared by Dimethyloctadec-9-en-1,18-dioat. This reaction will need reagent 20percent aq. NaOH and solvent ethanol. The reaction time is 2.5 hour(s). The yield is about 67%.

You can still convert the following datas into molecular structure:
(1)SMILES: OC(=O)CCCCCCCC=CCCCCCCCC(O)=O
(2)InChI: InChI=1/C18H32O4/c19-17(20)15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(21)22/h1-2H,3-16H2,(H,19,20)(H,21,22)
(3)InChIKey: SBLKVIQSIHEQOF-UHFFFAOYAK
(4)Std. InChI: InChI=1S/C18H32O4/c19-17(20)15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(21)22/h1-2H,3-16H2,(H,19,20)(H,21,22)
(5)Std. InChIKey: SBLKVIQSIHEQOF-UHFFFAOYSA-N

Product Name

8-Hexadecene-1,16-dicarboxylic acid

Synthetic route

9-Octadecenedioic acid Specification

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