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Quality Control of [ 153559-48-9 ] Purity: 98% SDS Specification

COA

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Product Details of [ 153559-48-9 ]

CAS No. :	153559-48-9
Formula :	C₂₅H₃₀O₂
M.W :	362.50
SMILES Code :	COC(=O)C1=CC=C(C=C1)C(=C)C1=CC2=C(C=C1C)C(C)(C)CCC2(C)C
MDL No. :	MFCD16620614
InChI Key :	VSMOGQLTPWIBNI-UHFFFAOYSA-N
Pubchem ID :	10384066

Safety of [ 153559-48-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 153559-48-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	27
Num. arom. heavy atoms	12
Fraction Csp3	0.4
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	113.69
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	4.45
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	7.93
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	6.19
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	5.47
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	7.17
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	6.24

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-7.15
Solubility	0.0000258 mg/ml ; 0.0000000711 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-8.33
Solubility	0.00000169 mg/ml ; 0.0000000046 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-8.41
Solubility	0.00000141 mg/ml ; 0.0000000039 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble

Pharmacokinetics

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	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-2.88 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.26

Application In Synthesis of [ 153559-48-9 ]

* 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 [ 153559-48-9 ]
Downstream synthetic route of [ 153559-48-9 ]

[ 153559-48-9 ] Synthesis Path-Upstream 1~17

1
[ 1779-49-3 ]
[ 153559-45-6 ]
[ 153559-48-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium amide In tetrahydrofuran	Rectangular plates of compound 35 were found suitable for X-ray diffraction, and a study was conducted. To complete the synthesis of bexarotene, the Friedel-Crafts acylation of 35, by crude mono-methyl-terephthaloyl chloride (36), gave ketone (37) which was converted to alkene ester(38) by a Wittig reaction, and ester 38 was saponified by potassium hydroxide followed by acidification with aqueous hydrochloric acid to give bexarotene (39) (Scheme 2).

References: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 19, p. 5950 - 5966.
[2] Patent: WO2011/103321, 2011, A1, . Location in patent: Page/Page column 19.
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2930 - 2941.
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 7, p. 701 - 712.
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3368 - 3383.

2
[ 67-56-1 ]
[ 153559-49-0 ]
[ 153559-48-9 ]

References: [1] Journal of Controlled Release, 2018, vol. 286, p. 10 - 19.

3
[ 169126-64-1 ]
[ 199188-36-8 ]
[ 153559-48-9 ]

References: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782.

4
[ 1779-49-3 ]
[ 153559-45-6 ]
[ 1349659-53-5 ]
[ 1349659-55-7 ]
[ 1349659-56-8 ]
[ 1349659-57-9 ]
[ 153559-48-9 ]

References: [1] Patent: WO2011/141928, 2011, A1, . Location in patent: Page/Page column 19.

5
[ 6683-48-3 ]
[ 153559-48-9 ]

References: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782.
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3368 - 3383.
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 7, p. 701 - 712.
[4] Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2930 - 2941.
[5] Patent: WO2011/103321, 2011, A1, .

6
[ 153559-49-0 ]
[ 74-88-4 ]
[ 153559-48-9 ]

References: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9785 - 9789[2] Angew. Chem., 2018, vol. 130, # 31, p. 9933 - 9937,5.

7
[ 110-03-2 ]
[ 153559-48-9 ]

References: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782.
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2930 - 2941.
[3] Patent: WO2011/103321, 2011, A1, .

8
[ 6223-78-5 ]
[ 153559-48-9 ]

References: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782.
[2] Patent: WO2011/103321, 2011, A1, .

9
[ 7377-26-6 ]
[ 153559-48-9 ]

References: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3368 - 3383.

10
[ 29020-85-7 ]
[ 153559-48-9 ]

References: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 7, p. 701 - 712.

11
[ 5455-94-7 ]
[ 153559-48-9 ]

References: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 7, p. 701 - 712.

12
[ 167958-79-4 ]
[ 153559-48-9 ]

References: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 7, p. 701 - 712.

13
[ 167958-78-3 ]
[ 153559-48-9 ]

References: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 7, p. 701 - 712.

14
[ 3609-53-8 ]
[ 153559-48-9 ]

References: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782.

15
[ 119999-22-3 ]
[ 153559-48-9 ]

References: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782.

16
[ 1679-64-7 ]
[ 1349659-56-8 ]
[ 153559-48-9 ]

References: [1] Patent: WO2011/141928, 2011, A1, .

17
[ 6683-48-3 ]
[ 1349659-56-8 ]
[ 1349659-57-9 ]
[ 153559-48-9 ]

References: [1] Patent: WO2011/141928, 2011, A1, .

[ 153559-48-9 ] Synthesis Path-Downstream 1~30

1
[ 1779-49-3 ]
[ 153559-45-6 ]
[ 153559-48-9 ]

Yield	Reaction Conditions	Operation in experiment
69%		Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed PPh3MeBr (1715 mg, 4.80 mmol, 2.50 eq.), THF (10 ml_). This was followed by the addition of KHDMS (1 M) (5.1 ml_, 5.1 1 mmol, 2.66 eq.) dropwise with stirring at -30C. The resulting solution was stirred for 30 min at 0C. To this was added a solution of methyl 4-[(3, 5, 5, 8, 8-pentamethyl-5, 6, 7, 8-tetrahydronaphthalen-2-yl) carbonyl] benzoate (700 mg, 1.92 mmol, 1.00 eq.) in THF (7 ml_) dropwise with stirring at -30C. The resulting solution was stirred for 1 h at 0C. The reaction was then quenched by the addition of 20 ml_ of water at 0C. The resulting solution was extracted with 2x20 ml_ of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1 c20 ml_ of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/10). This resulted in 480 mg (69%) of methyl 4-[1-(3, 5,5,8, 8-pentamethyl-5, 6,7,8- tetrahydronaphthalen-2-yl)ethenyl]benzoate as a light yellow solid.
66%	With sodium amide; In tetrahydrofuran;	Rectangular plates of compound 35 were found suitable for X-ray diffraction, and a study was conducted. To complete the synthesis of bexarotene, the Friedel-Crafts acylation of 35, by crude mono-methyl-terephthaloyl chloride (36), gave ketone (37) which was converted to alkene ester(38) by a Wittig reaction, and ester 38 was saponified by potassium hydroxide followed by acidification with aqueous hydrochloric acid to give bexarotene (39) (Scheme 2).

References: [1]Patent: WO2019/169270,2019,A1 .Location in patent: Paragraph 0141; 0143.
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 5950 - 5966.
[3]Patent: WO2011/103321,2011,A1 .Location in patent: Page/Page column 19.
[4]Journal of Medicinal Chemistry,1994,vol. 37,p. 2930 - 2941.
[5]Journal of labelled compounds and radiopharmaceuticals,1995,vol. 36,p. 701 - 712.
[6]Journal of Medicinal Chemistry,1995,vol. 38,p. 3368 - 3383.

2
[ 153559-48-9 ]
[ 153559-49-0 ]

Yield	Reaction Conditions	Operation in experiment
78%		Rectangular plates of compound 35 were found suitable for X-ray diffraction, and a study was conducted. To complete the synthesis of bexarotene, the Friedel-Crafts acylation of 35, by crude mono-methyl-terephthaloyl chloride (36), gave ketone (37) which was converted to alkene ester(38) by a Wittig reaction, and ester 38 was saponified by potassium hydroxide followed by acidification with aqueous hydrochloric acid to give bexarotene (39) (Scheme 2).
		Example 3: Preparation of bexaroteneTo suspension of methyl 4-[l-(5,6,7,8-tetrahydro-3, 5,5,8, 8-pentamethyl-2-naphthalenyl)-l- ethenyljbenzoate (100 g) in methanol (1000 ml), 5N aqueous potassium hydroxide (170 ml) was added at 25-30C and the reaction mixture was refluxed for 8 hours. After completion of reaction (monitored by HPLC), reaction mass was cooled to 35-40 C and washed with 50% ethyl acetate: n-heptane mixture (2 x 500 ml). The organic layer was discarded and the aqueous layer was cooled to 10-15 C. Thereafter pH of aqueous layer was adjusted to 1-2 by addition of concentrated hydrochloric acid (100 ml). The resulting mixture was then stirred at 20-25C, stirred for 1 hour and precipitated solid was filtered. The resulting solid was slurry washed with demineralized water (100 ml), centrifuged and dried to give 84.6 g of title compound having purity 98.89 %, none of the impurities C, D, E, F were detected by HPLC

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2930 - 2941.
[2]Journal of Medicinal Chemistry,1995,vol. 38,p. 3368 - 3383.
[3]Journal of labelled compounds and radiopharmaceuticals,1995,vol. 36,p. 701 - 712.
[4]Journal of Medicinal Chemistry,2009,vol. 52,p. 5950 - 5966.
[5]Patent: WO2011/103321,2011,A1 .Location in patent: Page/Page column 19.
[6]Journal of Organic Chemistry,2001,vol. 66,p. 5772 - 5782.
[7]Patent: WO2011/141928,2011,A1 .Location in patent: Page/Page column 19.

3
[ 75-11-6 ]
[ 153559-48-9 ]
methyl 4-<1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl>benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%		Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed Et2Zn (1M) (1.4 ml_, 1.4 mmol, 10.00 eq.), DCM (2 ml_). This was followed by the addition of TFA (157 mg, 1.39 mmol, 10.00 eq.) dropwise with stirring at 0C. The resulting solution was stirred for 30 min at 0C. To this was added CH2I2 (370 mg, 1.4 mmol, 10.00 equiv) dropwise with stirring at 0C. The resulting solution was stirred for 30 min at 0C. To the mixture was added a solution of methyl 4-[1-(3,5,5,8,8-pentamethyl- 5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoate (50 mg, 0.14 mmol, 1.00 equiv) in DCM (1 ml_) dropwise with stirring at 0C. The resulting solution was stirred for 2 h at room temperature. The reaction was then quenched by the addition of 20 mL of water at 0C. The solid was filtered out. The resulting solution was extracted with 2x20 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 1 c20 ml of brine and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/10). This resulted in 10 mg (19%) of methyl 4-[1-(3, 5,5,8, 8-pentamethyl-5, 6,7, 8-tetrahydronaphthalen-2- yl)cyclopropyl]benzoate as a white solid.

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3146 - 3155.
[2]Patent: WO2019/169270,2019,A1 .Location in patent: Paragraph 0141; 0144.

4
[ 153559-48-9 ]
methyl 4-<2-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)oxiranyl>benzoate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3146 - 3155.

5
[ 169126-64-1 ]
[ 199188-36-8 ]
[ 153559-48-9 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5772 - 5782.

6
[ 110-03-2 ]
[ 153559-48-9 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5772 - 5782.
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 2930 - 2941.
[3]Patent: WO2011/103321,2011,A1 .

7
[ 6223-78-5 ]
[ 153559-48-9 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5772 - 5782.
[2]Patent: WO2011/103321,2011,A1 .
[3]Patent: WO2019/169270,2019,A1 .

8
[ 3609-53-8 ]
[ 153559-48-9 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5772 - 5782.

9
[ 6683-48-3 ]
[ 153559-48-9 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5772 - 5782.
[2]Journal of Medicinal Chemistry,1995,vol. 38,p. 3368 - 3383.
[3]Journal of labelled compounds and radiopharmaceuticals,1995,vol. 36,p. 701 - 712.
[4]Journal of Medicinal Chemistry,1994,vol. 37,p. 2930 - 2941.
[5]Patent: WO2011/103321,2011,A1 .
[6]Patent: WO2019/169270,2019,A1 .

10
[ 119999-22-3 ]
[ 153559-48-9 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5772 - 5782.

11
C₁₀H₁₁C₅H₁₀B(C₃H₇O)2 [ No CAS ]
[ 153559-48-9 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5772 - 5782.

12
[ 7377-26-6 ]
[ 153559-48-9 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3368 - 3383.

13
[ 153559-48-9 ]
LGD₁₂₆₈ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3146 - 3155.
[2]Patent: WO2019/169270,2019,A1 .

14
[ 153559-48-9 ]
4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)epoxy]benzoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3146 - 3155.

15
[ 29020-85-7 ]
[ 153559-48-9 ]