Octadecanoic acid, 9,10-epoxy-, cis- supplier

Name
CIS-9,10-EPOXYSTEARIC ACID
EINECS
CAS No. 24560-98-3
Article Data69
CAS DataBase
Density 0.956g/cm³
Solubility
Melting Point 58-60°C
Formula C18H34 O3
Boiling Point 422.9°Cat760mmHg
Molecular Weight 298.466
Flash Point 141.1°C
Transport Information
Appearance
Safety Questionable carcinogen with experimental tumorigenic data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Octadecanoicacid, 9,10-epoxy-, cis- (8CI); Oxiraneoctanoic acid, 3-octyl-, (2R,3S)-rel-(9CI); Oxiraneoctanoic acid, 3-octyl-, cis-; (?à)-cis-9,10-Epoxystearic acid; Epoxyoleic acid;cis-9,10-Epoxyoctadecanoic acid; cis-9,10-Epoxystearic acid;cis-DL-9,10-Epoxystearic acid
PSA 49.83000
LogP 5.31970

Synthetic route

: 2500-59-6, 2566-91-8, 6084-76-0, 38003-69-9, 38003-75-7, 38003-77-9, 79854-41-4, 112244-28-7
(Z)-9,10-epoxyoctadecanoic acid methyl ester

: 24560-98-3
cis-9,10-epoxystearic acid

Conditions

Conditions	Yield
With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; for 16h; Inert atmosphere;	72%
With lithium hydroxide In tetrahydrofuran at 0 - 20℃;	52%
With potassium hydroxide; ethanol
With methanol; potassium hydroxide

: 79-21-0
peracetic acid

: 112-80-1
cis-Octadecenoic acid

: 24560-98-3
cis-9,10-epoxystearic acid

Conditions

Conditions	Yield
With acetic acid

: 93-59-4
Perbenzoic acid

: 112-80-1
cis-Octadecenoic acid

: 24560-98-3
cis-9,10-epoxystearic acid

Conditions

Conditions	Yield
With acetone
at 0 - 5℃;

: 112-80-1
cis-Octadecenoic acid

: 24560-98-3
cis-9,10-epoxystearic acid

Conditions

Conditions	Yield
With Perbenzoic acid; diethyl ether
With Perbenzoic acid; chloroform
With water; hypochloric acid und anschl. mit wss. KOH;

: 112-80-1
cis-Octadecenoic acid

: 100-52-7
benzaldehyde

: 24560-98-3
cis-9,10-epoxystearic acid

Conditions

Conditions	Yield
With acetone Irradiation.mit UV-Licht und Durchleiten von Luft;
With oxygen Irradiation.mit UV-Licht;

: 112-80-1
cis-Octadecenoic acid

A: 120-87-6
Dihydroxystearic Acid

B: 2632-61-3
9-Chlor-10-hydroxy-octadecansaeure

: 24560-98-3
cis-9,10-epoxystearic acid

Conditions

Conditions	Yield
With hydrogenchloride; hypochloric acid Mechanism; fatty acids and lipids;

...Expand

: 112-80-1
cis-Octadecenoic acid

peroxynonanoic acid: peroxynonanoic acid

: 24560-98-3
cis-9,10-epoxystearic acid

Conditions

Conditions	Yield
With benzene

: 120-87-6, 2391-05-1, 3639-32-5, 10067-09-1, 20831-62-3, 20831-68-9, 38003-70-2
threo-9,10-dihydroxyoctadecanoic acid

: 24560-98-3
cis-9,10-epoxystearic acid

B threo-9,10-dihydroxy-octadecanoic acid: threo-9,10-dihydroxy-octadecanoic acid

Conditions

Conditions	Yield
With hydrogenchloride at 160℃; anschl. Erhitzen mit wss. Alkalilauge;

: 112-80-1
cis-Octadecenoic acid

hydroperoxyoctadecenoic acid methyl ester: hydroperoxyoctadecenoic acid methyl ester

: 120-87-6, 2391-05-1, 3639-32-5, 10067-09-1, 20831-62-3, 20831-68-9, 38003-70-2
threo-9,10-dihydroxyoctadecanoic acid

: 24560-98-3
cis-9,10-epoxystearic acid

Conditions

Conditions	Yield
at 90℃; bei 3-taegigem Erwaermen;

...Expand

: 112-80-1
cis-Octadecenoic acid

cobalt oleate: cobalt oleate

: 24560-98-3
cis-9,10-epoxystearic acid

B lower-melting (trans-)9.10-epoxy-stearic acid: lower-melting (trans-)9.10-epoxy-stearic acid

Conditions

Conditions	Yield
at 65℃;

...Expand

: 120-87-6, 2391-05-1, 3639-32-5, 10067-09-1, 20831-62-3, 20831-68-9, 38003-70-2
erythro-9,10-dihydroxystearic acid

: 24560-98-3
cis-9,10-epoxystearic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl; glycerol / 160 °C / Kochen des Reaktionsprodukts mit verd. Alkalilauge und Erhitzen der erhaltenen cis-9.10-Epoxy-stearinsaeure mit 7n-KOH auf 17grad 2: HCl / 160 °C / anschl. Erhitzen mit wss. Alkalilauge View Scheme

: 112-79-8
Elaidic acid

: 24560-98-3
cis-9,10-epoxystearic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: peroxybenzoic acid; chloroform / anschliessende Hydrolyse 2: HCl; glycerol / 160 °C / Kochen des Reaktionsprodukts mit verd. Alkalilauge und Erhitzen der erhaltenen cis-9.10-Epoxy-stearinsaeure mit 7n-KOH auf 17grad 3: HCl / 160 °C / anschl. Erhitzen mit wss. Alkalilauge View Scheme

: 112-62-9
Methyl oleate

: 24560-98-3
cis-9,10-epoxystearic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 15.17 h / 0 - 23 °C / Inert atmosphere 2: lithium hydroxide monohydrate / tetrahydrofuran; water / 16 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C 2: lithium hydroxide / tetrahydrofuran / 0 - 20 °C View Scheme

: 24560-98-3
cis-9,10-epoxystearic acid

: 10067-09-1
threo-9,10-dihydroxystearic acid

Conditions

Conditions	Yield
With rabbit liver microsomal epoxide hydrolase In water at 37℃; Rate constant; saturation rates; enantioselectivity;	90%
With rabbit liver microsomal epoxide hydrolase In water at 37℃; for 20h;	90%

: 24560-98-3
cis-9,10-epoxystearic acid

: 120-87-6, 2391-05-1, 3639-32-5, 10067-09-1, 20831-62-3, 20831-68-9, 38003-70-2
dl-threo-9,10-dihydroxyoctadecanoic acid

Conditions

Conditions	Yield
In acetic acid for 3h; Heating;	72%

: 24560-98-3
cis-9,10-epoxystearic acid

: C18H32O3

Conditions

Conditions	Yield
Stage #1: cis-9,10-epoxystearic acid With Zn(2,2,6,6-tetramethylpiperidine)2*2LiCl; zinc(II) chloride In tetrahydrofuran at -40℃; for 1.5h; Inert atmosphere; Sealed tube; Stage #2: With bis(η3-allyl-μ-chloropalladium(II)); Allyl acetate In tetrahydrofuran at -40 - 60℃; for 12h; Inert atmosphere; Sealed tube; diastereoselective reaction;	72%

: 67-56-1
methanol

: 24560-98-3
cis-9,10-epoxystearic acid

: 2500-59-6, 2566-91-8, 6084-76-0, 38003-69-9, 38003-75-7, 38003-77-9, 79854-41-4, 112244-28-7
(Z)-9,10-epoxyoctadecanoic acid methyl ester

Conditions

Conditions	Yield
With trifluoroacetic anhydride In benzene at 25℃; for 0.666667h;	12%

: 24560-98-3
cis-9,10-epoxystearic acid

: 2632-61-3, 13985-22-3, 13985-23-4
(+/-)-threo-9-chloro-10-hydroxy-octadecanoic acid

Conditions

Conditions	Yield
With hydrogenchloride; diethyl ether
With hydrogenchloride In diethyl ether

: 24560-98-3
cis-9,10-epoxystearic acid

: 55763-88-7, 55763-89-8, 94376-80-4
(+/-)-threo-9-bromo-10-hydroxy-octadecanoic acid

Conditions

Conditions	Yield
With diethyl ether; hydrogen bromide
With hydrogen bromide In diethyl ether

: 24560-98-3
cis-9,10-epoxystearic acid

: 5286-65-7, 5286-66-8, 20831-60-1, 20831-61-2, 94306-44-2
threo-10-hydroxy-9-iodo-octadecanoic acid

Conditions

Conditions	Yield
With diethyl ether; hydrogen iodide

: 24560-98-3
cis-9,10-epoxystearic acid

: 120-87-6, 2391-05-1, 3639-32-5, 10067-09-1, 20831-62-3, 20831-68-9, 38003-70-2
threo-9,10-dihydroxyoctadecanoic acid

Conditions

Conditions	Yield
With dimethyl sulfoxide
(i) AcOH, (ii) aq. NaOH; Multistep reaction;
With perchloric acid In tetrahydrofuran; water for 12h;
With sulfuric acid; water In tetrahydrofuran at 20℃; for 72h;

: 24560-98-3
cis-9,10-epoxystearic acid

: 2632-62-4, 13985-24-5, 13985-25-6
(+/-)-threo-10-chloro-9-hydroxy-octadecanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In diethyl ether

: 24560-98-3
cis-9,10-epoxystearic acid

: 55763-86-5, 55763-87-6, 94376-81-5
(+/-)-threo-10-bromo-9-hydroxy-octadecanoic acid

Conditions

Conditions	Yield
With hydrogen bromide In diethyl ether

: 24560-98-3
cis-9,10-epoxystearic acid

: 215252-53-2
methyl (9R,10R)-9,10-dihydroxyoctadecanoate

Conditions

Conditions	Yield
(i) (enzymatic hydrolysis), (ii) (esterification); Multistep reaction;

: 24560-98-3
cis-9,10-epoxystearic acid

: 98860-62-9
9,10-bis-hydroxyimino-octadecanoic acid

Conditions

Conditions	Yield
(i) aq. HCl, Et2O, (ii) CrO3, acetone, (iii) NH2OH, EtOH; Multistep reaction;

: 7664-93-9
sulfuric acid

: 24560-98-3
cis-9,10-epoxystearic acid

lower-melting θ-ι-dioxy-stearic acid: lower-melting θ-ι-dioxy-stearic acid

: 24560-98-3
cis-9,10-epoxystearic acid

KOH-solution: KOH-solution

lower-melting θ-ι-dioxy-stearic acid: lower-melting θ-ι-dioxy-stearic acid

: 24560-98-3
cis-9,10-epoxystearic acid

polycondenzation products: polycondenzation products

Conditions

Conditions	Yield
Erhitzen der Schmelze;

: 7664-41-7
ammonia

: 7732-18-5
water

: 24560-98-3
cis-9,10-epoxystearic acid

threo(?)-9-amino-10-hydroxy-octadecanoic acid: threo(?)-9-amino-10-hydroxy-octadecanoic acid

...Expand

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 24560-98-3
cis-9,10-epoxystearic acid

: cis-9,10-epoxystearic acid succinimidyl ester

Conditions

Conditions	Yield
With diisopropyl-carbodiimide In tetrahydrofuran; dichloromethane at 4℃;

: 24560-98-3
cis-9,10-epoxystearic acid

: 6064-72-8, 10411-46-8, 13985-35-8
(+/-)-threo-10-chloro-9-hydroxy-octadecanoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / diethyl ether 2: diethyl ether View Scheme

Octadecanoic acid, 9,10-epoxy-, cis- Chemical Properties

Molecule structure of Octadecanoic acid, 9,10-epoxy-, cis- (CAS NO.24560-98-3):

IUPAC Name: 8-[(2S,3R)-3-Octyloxiran-2-yl]octanoic acid
Molecular Weight: 298.46076 g/mol
Molecular Formula: C₁₈H₃₄O₃
Density: 0.956 g/cm³
Boiling Point: 422.9 °C at 760 mmHg
Flash Point: 141.1 °C
Index of Refraction: 1.467
Molar Refractivity: 86.64 cm³
Molar Volume: 312.1 cm³
Polarizability: 34.34×10^-24 cm³
Surface Tension: 37.4 dyne/cm
Enthalpy of Vaporization: 74.27 kJ/mol
Vapour Pressure: 2.46E-08 mmHg at 25 °C
Storage Temp.: −20 °C
XLogP3-AA: 6.1
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 15
Exact Mass: 298.250795
MonoIsotopic Mass: 298.250795
Topological Polar Surface Area: 49.8
Heavy Atom Count: 21
Complexity: 265
Defined Atom StereoCenter Count: 2
Canonical SMILES: CCCCCCCCC1C(O1)CCCCCCCC(=O)O
Isomeric SMILES: CCCCCCCC[C@@H]1[C@@H](O1)CCCCCCCC(=O)O
InChI: InChI=1S/C18H34O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h16-17H,2-15H2,1H3,(H,19,20)/t16-,17+/m1/s1
InChIKey of Octadecanoic acid, 9,10-epoxy-, cis- (CAS NO.24560-98-3): IMYZYCNQZDBZBQ-SJORKVTESA-N

Octadecanoic acid, 9,10-epoxy-, cis- Safety Profile

Questionable carcinogen with experimental tumorigenic data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
RTECS: RG1400000

Octadecanoic acid, 9,10-epoxy-, cis- Specification

Octadecanoic acid, 9,10-epoxy-, cis- (CAS NO.24560-98-3) is also called (+-)-cis-9,10-Epoxystearic acid ; 5-18-06-00055 (Beilstein Handbook Reference) ; BRN 0085932 ; Epoxyoleic acid ; Oxiraneoctanoic acid, 3-octyl-, cis- ; cis-3-Octyloxirane octanoic acid ; cis-9,10-Epoxystearic acid ; cis-DL-9,10-Epoxystearic acid ; Oxiraneoctanoic acid, 3-octyl-, (2R,3S)-rel- .

Product Name

CIS-9,10-EPOXYSTEARIC ACID

Synthetic route

Octadecanoic acid, 9,10-epoxy-, cis- Chemical Properties

Octadecanoic acid, 9,10-epoxy-, cis- Safety Profile

Octadecanoic acid, 9,10-epoxy-, cis- Specification

Related Products

Hot Products