Structure of 8-Carboxyoctanol
CAS No.: 3788-56-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 3788-56-5 |
Formula : | C9H18O3 |
M.W : | 174.24 |
SMILES Code : | OCCCCCCCCC(O)=O |
MDL No. : | MFCD00792445 |
InChI Key : | AFZMICRBFKZNIH-UHFFFAOYSA-N |
Pubchem ID : | 138052 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.89 |
Num. rotatable bonds | 8 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 48.31 |
TPSA ? Topological Polar Surface Area: Calculated from |
57.53 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.83 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.43 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.79 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.4 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.67 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.42 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.66 |
Solubility | 37.8 mg/ml ; 0.217 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.21 |
Solubility | 10.9 mg/ml ; 0.0623 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.91 |
Solubility | 2.13 mg/ml ; 0.0122 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.06 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.6 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With sulfuric acid; for 5.0h;Reflux; | To a solution of <strong>[3788-56-5]9-hydroxynonanoic acid</strong> (2) (1.0 g, 5.74 mmol, 1.0 eq) in methanol (30 mL) was added sulfuric acid (1 mL). The reaction mixture was heated to reflux for 5 h. Then the mixture was concentrated under reduced pressure and the residue was diluted with water (15 mL) and ethyl acetate (10 mL). The aqueous layer was back-extracted with additional ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SC>4. The solvent was removed under reduced pressure and the crude was purified by column chromatography (PE/EA (petroleum ether/ethyl acetate) = 10: 1) to give methyl 9-hydroxynonanoate (3) (500 mg, 46%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With sodium tetrahydroborate; In 1,4-dioxane; at 0 - 20℃; | A solution of 0.8 g (4.65 mmol) of 7 in dioxane (8 mL) was treated with 0.2 g (50 mmol) of sodium borohydride in small portions with cooling in ice-water. the mixture then stirred at room temperature overnight, until TLC monitoring indicated completion and poured over crushed ice. Acidify the mixture by HCl 37% to consume the excess NaBH4. The product was extracted with 3 ×40 mL ether and The organic layers were combined, washed with water (1 × 30 mL), brine (1 × 30mL), and dried over Na2SO4. The solvent removed under reduced pressure and then purified by column chromatography (1:1 hexanes: ethyl acetate) to give pure 1 as a white solid (460 g, 2.64 mmol, 56 %). m.p. 51C. IR spectrum (cm-1): 3334, 2931, 2852, 1692 cm-1. 1H NMR (300 MHz,CDCl3) delta 6.07 (m, 2H, CH2OH and COOH), 3.63 (t, 2H, J = 6.6 Hz, CH2OH), 2.33 (t, 2H, J = 7.5Hz, CH2COOH), 1.62 (m, 4H, CH2CH2CH2OH and CH2CH2COOH), 1.25-1.32 (m, 8H, CH2). 13CNMR (75 MHz, CDCl3): delta 179.2 (s, COOH), 63.5 (t, CH2OH), 34.3, 32.9, 29.5, 29.3, 26.0, 25.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Any omega-hydroxy acid which falls within Formula V may be synthesised according to inventive processes A and B. Examples of omega-hydroxy acids that may be synthesised include, but are not limited to: 6-hydroxy hexanoic acid 7-hydroxy heptanoic acid 8-hydroxy octanoic acid 9-hydroxy nonanoic acid 10-hydroxy decanoic acid 11-hydroxy undecanoic acid 2,25-dihydroxy dihydroxy pentacosanoic acid 12-hydroxy dodecanoic acid 14-hydroxy tetradecanoic acid ... |