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[ CAS No. 112-80-1 ] {[proInfo.proName]}

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Chemical Structure| 112-80-1
Chemical Structure| 112-80-1
Structure of 112-80-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 112-80-1 ]

CAS No. :112-80-1 MDL No. :MFCD00064242
Formula : C18H34O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZQPPMHVWECSIRJ-KTKRTIGZSA-N
M.W : 282.46 Pubchem ID :445639
Synonyms :
9-cis-Octadecenoic acid;9Z-Octadecenoic acid;D 100;C18:1 (cis-9) Fatty acid;Octadecenoic acid (cis-9);Elaidoic acid;9-Octadecenoic Acid;Oleate

Calculated chemistry of [ 112-80-1 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 15
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 89.94
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -2.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.27
Log Po/w (XLOGP3) : 7.64
Log Po/w (WLOGP) : 6.11
Log Po/w (MLOGP) : 4.57
Log Po/w (SILICOS-IT) : 5.95
Consensus Log Po/w : 5.71

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -5.41
Solubility : 0.00109 mg/ml ; 0.00000385 mol/l
Class : Moderately soluble
Log S (Ali) : -8.26
Solubility : 0.00000154 mg/ml ; 0.0000000055 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -5.39
Solubility : 0.00114 mg/ml ; 0.00000404 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.07

Safety of [ 112-80-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 112-80-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 112-80-1 ]
  • Downstream synthetic route of [ 112-80-1 ]

[ 112-80-1 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 1008-88-4 ]
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  • [ 33421-40-8 ]
  • [ 87109-10-2 ]
Reference: [1] Patent: US4386209, 1983, A,
  • 2
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  • [ 33421-40-8 ]
  • [ 87109-10-2 ]
Reference: [1] Patent: US4386209, 1983, A,
  • 3
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  • [ 504-40-5 ]
  • [ 555-43-1 ]
  • [ 2846-04-0 ]
Reference: [1] Chemische Berichte, 1903, vol. 36, p. 2767[2] Chem. Zentralbl., 1904, vol. 75, # II, p. 413
  • 4
  • [ 112-80-1 ]
  • [ 627-91-8 ]
  • [ 1120-34-9 ]
Reference: [1] Journal of the Chemical Society, 1953, p. 2393,2397
  • 5
  • [ 107-97-1 ]
  • [ 112-80-1 ]
  • [ 4316-73-8 ]
  • [ 110-25-8 ]
Reference: [1] Patent: US5710295, 1998, A,
  • 6
  • [ 122-32-7 ]
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  • [ 4704-94-3 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 16 - 24
  • 7
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  • [ 3937-56-2 ]
Reference: [1] Polymer, 2011, vol. 52, # 20, p. 4503 - 4516
  • 8
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  • [ 4494-16-0 ]
YieldReaction ConditionsOperation in experiment
47% at 45℃; for 72 h; Inert atmosphere Compound 4 was prepared according to a literature procedure.2 Oleic acid (89 g (90percent), 0.315 mol)was transferred into a 250-mL three-necked round-bottomed flask via syringe and out gassed with N2 for 0.5 h. 1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene) (dichlorophenylmethylene)-tricyclohexylphosphine) ruthenium (267 mg, 0.315 mmol), 2nd generation Grubbs catalyst, was then added. The reaction mixture was stirred with a mechanical stirrer and heated at 45°C, and after ~5min the diacid began to precipitate from the reaction mixture. After 3 days stirring the crude product was quenched with ethyl vinyl ether (40 mL), and excess ether was removed under reduced pressure. The residue was recrystallized several times from a mixture of hexane (300 mL) and ethylacetate (50 mL) to give pure 4 as a white solid (23.5 g, 7.52 mmol, 47 percent). m.p. 97–98 °C. 1H NMR(300 MHz, CD3OD): δ 5.39 (m, 2H, –CH=CH–), 2.27 (t, 4H, J = 7.35 and 7.35 Hz, –CH2–COOH), 1.97 (m, 4H), 1.60 (m, 4H), 1.32 (m, 16H, –CH2–). 13C NMR (75 MHz, CD3OD): δ181.0 (s, –COOH), 131.6 (d, 2C, –CH=CH–), 35.1, 33.7, 30.8, 30.4, 30.3, 30.2, 26.2.
29.75 g at 45℃; for 24 h; Inert atmosphere Oleic acid (76 g) was transferred into a 250 mL three-necked round bottom flask and stirred at 45° C. under nitrogen gas for 0.5 hours. Grubbs 2nd generation catalyst (85 mg) was added. The reaction mixture was stirred at 45° C. for around 5 min. The diacid began to precipitate from the reaction mixture. The reaction was kept at this temperature for 24 hours, and then quenched with ethyl vinyl ether (15 mL). The excess ether was removed under reduced pressure. The residue was purified by recrystallization from ethyl acetate and hexanes (1:2) to give 29.75 g of product as a white solid.
Reference: [1] Synthetic Communications, 2014, vol. 44, # 8, p. 1149 - 1154
[2] Patent: US2011/300590, 2011, A1, . Location in patent: Page/Page column 7
[3] Patent: US2015/321992, 2015, A1, . Location in patent: Paragraph 0050
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 26, p. 7589 - 7594[5] Angew. Chem., 2017, vol. 129, # 26, p. 7697 - 7702,6
  • 9
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YieldReaction ConditionsOperation in experiment
71%
Stage #1: at 45℃; for 24.08 - 72 h; Neat (no solvent)
Oleic acid ((3b), 89 g (90percent, 0.315 mol) was transferred into a 250 mL 3-neck round bottom flask via syringe and out-gassed with nitrogen gas for 0.5 h. 1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(dichlorophenylmethylene)(tricyclohexylphosphine)ruthenium (2, 267 mg, 0.315 mmol), a second generation Grubbs catalyst, was then added; no solvent was utilized. The reaction mixture was stirred with a mechanical stirrer and heated at 45° C. and after about 5 minutes a white precipitate formed. After 24 h reaction, about 10 mg of crude product was removed from the reaction mixture and transferred to a 2 mL dram vial. The crude diacid product (5b, eq. 1) was added to 1 mL of methanol and two drops of conc. sulfuric acid were added. The resulting mixture was heated at 80° C. for 0.5 h (Christie, W. W., Lipid analysis: Isolation, Separation, Identification, and Structural Analysis of Lipids, Oxford, N.Y. Pergamon Press (1982)). The reaction mixture was then quenched with 2 mL of 1M Na2CO3, extracted with diethyl ether (3.x.2 mL) and the combined ether layers washed with water (3.x.2 mL). The organic layer was dried with MgSO4, filtered, solvent removed under reduced pressure, and the methylated diacid 5b characterized by GC/MS: (retention time=14.2 min) and gave an [M]+ of m/z 340 (calc., [M]+ for 5b is m/z=340.26). The remainder of the crude product was quenched with ethyl vinyl ether (20 mL) and excess ether was removed under reduced pressure. The residue was recrystallized from a mixture of hexane (300 mL) and ethyl acetate (50 mL) twice to give pure 1,18-octadec-9-enedioic acid (5b, eq. 1) as a white solid, m. p., 97.5-98.5° C. (lit. m. p., 88° C. (Van Dam, P. B., et al., J. Am. Oil. Chem. Soc., 51: 389-391 (1974)). Isolated yield: 35 g (71percent). 1H NMR of 1,18-octadec-9-enedioic acid (CD3OD, 400 MHz): δ 5.39 (m, -CHCH-, 2H), 2.28 (t, J=7.2 Hz 7.6 Hz, -CH&2CO2H, 4H), 1.98 (m, 4H), 1.60 (m, 4H), 1.32 (m, 16H). 13C NMR (CD3OD, 100 MHz): δ 177.8 (s, CO2H), 131.6 (s, CHCH), 35.1 (s), 33.7 (s), 30.8 (s), 30.4 (s), 30.3 (s), 30.2 (s), 26.2 (s).
Reference: [1] JAOCS, Journal of the American Oil Chemists' Society, 2006, vol. 83, # 7, p. 629 - 634
[2] Patent: US7534917, 2009, B1, . Location in patent: Page/Page column Sheet 2/6; 6-8; 16; 18
[3] Patent: EP1251135, 2002, A2, . Location in patent: Page 16
[4] Journal of the American Chemical Society, 2012, vol. 134, # 33, p. 13716 - 13729
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Reference: [1] Patent: US2015/336871, 2015, A1, . Location in patent: Paragraph 0071-0081
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  • [ 4494-16-0 ]
  • [ 75039-83-7 ]
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Reference: [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1 - 8
  • 12
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Reference: [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1 - 8
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Reference: [1] Patent: EP1251135, 2002, A2, . Location in patent: Page 16-17
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