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: |
|
| 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 ... |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; water; | 9-Hydroxynonanoic acid (8; commercially available from Matrix Scientific Corporation, Post Office Box 25067, Columbia, S.C. 29224-5067) is oxidized to aldehyde 9 using catalytic 2,2,6,6-tetramethyl-piperidinoxyl free radical (TEMPO) and stoichiometric N-chlorosuccinimide (NCS) in a rapidly stirring mixture of CH2Cl2, water, and catalytic n-Bu4NHSO4. Conversion of 9 to cis-vinyl iodide 10 is effected using Ph3PCH2I2 and NaN(SiMe3)2 (NaHMDS) in THF/HMPA. Sonogishira coupling of 10 with (3S)-1-octyn-3-ol (11; commercially available from Aldrich Chemical Co., Post Office Box 355, Milwaukee, Wis. 53201) is accomplished using in HNEt2 as solvent using stoichiometric CuI and catalytic Cl2Pd(PPh3)2 provides enyne 2 (R=H). Treatment with CH2N2 in diethyl ether affords the methyl ester 2 (R=CH3), while treatment with Etl and DBU in acetone yields ethyl ester 2 (R=C2H5) |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 41.1% | With pyridine; thionyl chloride; potassium carbonate; In dichloromethane; | EXAMPLE 12 N-Methyl-9-(3,5-di-tert-butyl-4-hydroxyphenyl)thiononanohydroxamic acid (I12) STR22 A mixture of 1.02 g (5.85 mmol) of <strong>[3788-56-5]9-hydroxynonanoic acid</strong> (IV4), 1 ml of thionyl chloride, and a drop portion of pyridine was heated for 3 hours on a warm bath at 70 C. and the remainder thionyl chloride was evaporated under reduced pressure. A solution of the resulting residue in 20 ml of dichloromethane was treated with 20 ml of an aqueous solution of 530 mg (6.35 mmol) of methylhydroxylamine hydrochloride and 900 mg (6.5 mmol) of potassium carbonate according to the procedure shown in Example 10 to give N-methyl-9-chlorononanohydroxamic acid (V8), which was chromatographed on silica gel eluted with ether to give 534 mg of the pure compound (V8) as a pale yellow oil in 41.1% yield. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 100% | With acetic anhydride; In pyridine; | EXAMPLE 19 5-(8-Hydroxyoctyl)-2-(1-normon-2-yl) oxazole A 9-Hydroxynonanoic acid (8.7 g, 50 mmol) in pyridine (8.1 ml, 100 mmol) was treated with acetic anhydride (4.7 ml, 50 mmol) at below 20 C. for 2 h. The mixture was poured onto ice and acidified. Two ether extractions gave 9-acetoxynonanoic acid as a colourless oil (10.8 g, 100%); deltaH (CDCl3) 10.0 (1H, s, CO2 H), 4.0 (2H, t, H9), 2.3 (2H, m, H2), 2.0 (3H, s, OAC), 1.1-1.8 (12H, m, H3-H8). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 99% | With sodium tetrahydroborate; water; In 1,4-dioxane; at 25℃; | To a solution of 9-methoxy-9-oxononanoic acid (1) (2.0 g, 9.89 mmol, 1.0 eq) in dioxane/water (v/v, 25mL/25 mL) was added NaBH4 (2.6 g, 70.27 mmol, 7.0 eq) in portions. The reaction mixture was stirred at 25 C for one night. Then the mixture was quenched by IN aqueous solution of hydrochloric acid at 0 C and extracted with dichloromethane (3 x 30 mL). The organic layers were dried over anhydrous Na2SC>4 and concentrated to give 9-hydroxynonanoic acid (2) (2.0 g, 99%) which was used directly to next step without purification. [0133] Step 2 -hydroxynonanoate reflux, 5 h, 46% |