[ CAS No. 4654-08-4 ]

Name: 4654-08-4|5-(4-Hydroxyphenyl)pentanoic acid|98%
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SKU: A191897
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Quality Control of [ 4654-08-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4654-08-4 ]

Product Details of [ 4654-08-4 ]

CAS No. :	4654-08-4	MDL No. :	MFCD04039777
Formula :	C₁₁H₁₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YSSJQFONKASLKM-UHFFFAOYSA-N
M.W :	194.23	Pubchem ID :	7016423
Synonyms :

Calculated chemistry of [ 4654-08-4 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	54.43
TPSA :	57.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.62
Log Po/w (XLOGP3) :	2.34
Log Po/w (WLOGP) :	2.19
Log Po/w (MLOGP) :	1.96
Log Po/w (SILICOS-IT) :	2.13
Consensus Log Po/w :	2.05

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.51
Solubility :	0.606 mg/ml ; 0.00312 mol/l
Class :	Soluble
Log S (Ali) :	-3.19
Solubility :	0.126 mg/ml ; 0.000649 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.82
Solubility :	0.295 mg/ml ; 0.00152 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.28

Safety of [ 4654-08-4 ]

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 [ 4654-08-4 ]

* 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 [ 4654-08-4 ]
Downstream synthetic route of [ 4654-08-4 ]

[ 4654-08-4 ] Synthesis Path-Upstream 1~19

1
[ 7508-04-5 ]
[ 4654-08-4 ]

Reference： [1] Journal of Organic Chemistry, 1948, vol. 13, p. 576,578
[2] Journal of the American Chemical Society, 1992, vol. 114, # 9, p. 3429 - 3441
[3] Bioscience, Biotechnology and Biochemistry, 1999, vol. 63, # 5, p. 958 - 960
[4] Organic and Biomolecular Chemistry, 2015, vol. 13, # 39, p. 9977 - 9983

2
[ 64201-30-5 ]
[ 4654-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 509 - 513

3
[ 50463-48-4 ]
[ 4654-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 509 - 513

4
[ 68486-77-1 ]
[ 4654-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 509 - 513

5
[ 129649-59-8 ]
[ 4654-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 509 - 513

6
[ 101268-18-2 ]
[ 4654-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2771 - 2782

7
[ 100-66-3 ]
[ 4654-08-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 39, p. 9977 - 9983

8
[ 108-55-4 ]
[ 4654-08-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 39, p. 9977 - 9983

9
[ 4609-10-3 ]
[ 4654-08-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 39, p. 9977 - 9983

10
[ 1929-29-9 ]
[ 4654-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2771 - 2782

11
[ 15823-04-8 ]
[ 4654-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2771 - 2782

12
[ 5406-18-8 ]
[ 4654-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2771 - 2782

13
[ 20401-88-1 ]
[ 4654-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2771 - 2782

14
[ 1316316-65-0 ]
[ 4654-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2771 - 2782

15
[ 4648-94-6 ]
[ 4654-08-4 ]

Reference： [1] Chemische Berichte, 1954, vol. 87, p. 345,348
[2] Chemische Berichte, 1955, vol. 88, p. 834,843

16
[ 47172-89-4 ]
[ 4654-08-4 ]

Reference： [1] Chemische Berichte, 1954, vol. 87, p. 345,348
[2] Chemische Berichte, 1955, vol. 88, p. 834,843

17
[ 199444-26-3 ]
[ 87-86-5 ]
[ 4654-08-4 ]

Reference： [1] Gazzetta Chimica Italiana, 1997, vol. 127, # 5, p. 269 - 272

18
[ 103856-01-5 ]
[ 4654-08-4 ]

Reference： [1] Archives of Biochemistry, 1945, vol. 7, p. 415,422

19
[ 2270-20-4 ]
[ 4654-08-4 ]

Reference： [1] Archives of Biochemistry, 1945, vol. 7, p. 415,422

[ 4654-08-4 ] Synthesis Path-Downstream 1~69

1
[ 4648-94-6 ]
[ 4654-08-4 ]

Reference： [1]Chemische Berichte,1954,vol. 87,p. 345,348

2
[ 4654-08-4 ]
5-(4-hydroxy-3,5-diiodo-phenyl)-valeric acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1948,vol. 13,p. 576,578

3
[ 7508-04-5 ]
[ 4654-08-4 ]

Reference： [1]Journal of Organic Chemistry,1948,vol. 13,p. 576,578
[2]Journal of the American Chemical Society,1992,vol. 114,p. 3429 - 3441
[3]Bioscience, Biotechnology and Biochemistry,1999,vol. 63,p. 958 - 960
[4]Organic and Biomolecular Chemistry,2015,vol. 13,p. 9977 - 9983

4
[ 64-17-5 ]
[ 4654-08-4 ]
[ 154044-13-0 ]

Reference： [1]Molecular Pharmacology,2006,vol. 70,p. 259 - 266
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 9977 - 9983

5
[ 501-97-3 ]
potash [ No CAS ]
[ 4654-08-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513

6
[ 4654-08-4 ]
4-(5-{2-[2-(3,5-dimethyl-phenyl)-1<i>H</i>-indol-3-yl]-ethylamino}-pentyl)-phenol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513

7
[ 4654-08-4 ]
4-(5-{2-[2-(3,4-dimethoxy-phenyl)-1<i>H</i>-indol-3-yl]-ethylamino}-pentyl)-phenol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513

8
[ 50463-48-4 ]
[ 4654-08-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513

9
[ 68486-77-1 ]
[ 4654-08-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513

10
[ 129649-59-8 ]
[ 4654-08-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513

11
[ 4654-08-4 ]
[ 142516-74-3 ]

Reference： [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879

12
[ 4654-08-4 ]
[ 154044-14-1 ]

Reference： [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879

13
[ 4654-08-4 ]
[ 197796-06-8 ]

Reference： [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879

14
[ 4654-08-4 ]
[ 197796-04-6 ]

Reference： [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879

15
[ 4654-08-4 ]
C₈₄H₁₀₀O₈ [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879

16
[ 4654-08-4 ]
C₉₀H₁₁₂O₈ [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879

17
[ 47172-89-4 ]
[ 4654-08-4 ]

Reference： [1]Chemische Berichte,1954,vol. 87,p. 345,348

18
[ 2270-20-4 ]
[ 4654-08-4 ]

Reference： [1]Archives of Biochemistry,1945,vol. 7,p. 415,422

19
[ 67-56-1 ]
[ 4654-08-4 ]
[ 64201-30-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sulfuric acid; In water; at 65℃;Inert atmosphere;	[0199] Equipment: 500 ml three-necked flask equipped with magnetic agitation and a refrigerant and placed under nitrogen scavenging-Oil bath. [0200] The <strong>[4654-08-4]5-(4-hydroxyphenyl)-pentanoic acid</strong> 1 (25 g) is put in solution in methanol (375 ml) before slowly pouring in a sulphuric acid solution (25 ml). The solution thus obtained is heated at 65 C. for the night. [0201] The advancement of the reaction is monitored by TLC (eluent: heptane/ethyl acetate: 1/1). After a night of agitation under these conditions, the disappearance of the starting acid 1 is observed in favour of a less polar product. [0202] The reaction medium is concentrated dry under reduced pressure. The residue obtained is taken up by dichloromethane (300 ml). The heterogeneous medium is neutralised and basified, carefully, with a saturated sodium hydrogenocarbonate solution (pH 8-9). The aqueous phase is then extracted three times with dichloromethane. Once collected together, the organic phases are washed once with a saturated sodium chloride solution, dried on magnesium sulphate, filtered and then concentrated under reduced pressure in order to provide a pinkish oil (27 g). [0203] Yield 99%.
99%	With sulfuric acid; at 65℃;	Step 1: Esterification (0419) Equipment: 500 ml Three-Necked Flask Equipped with Magnetic Agitation, Coolant and Placed Under a Stream of Nitrogen-Oil Bath. (0420) <strong>[4654-08-4]5-(4-hydroxyphenyl)-pentanoic acid</strong> 1 (25 g) is placed in solution in methanol (37 5 ml) before slow pouring of sulfuric acid (25 ml). The solution obtained is heated to 65 C. overnight. The progress of the reaction is monitored by TLC (eluting with heptane/ethyl Acetate 1:1). After overnight agitation under these conditions the starting acid 1 is seen to disappear to the benefit of a less polar product. (0421) The reaction medium is concentrated to dryness under reduced pressure. The residue obtained is re-dissolved in dichloromethane (300 ml). The heterogeneous medium is neutralised and basified with precaution with saturated sodium hydrogen carbonate solution (pH 8-9). The aqueous phase is then extracted three times with dichloromethane. Once combined, the organic phases are washed once with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford a pinkish oil (27 g). (0422) Yield: 99%

Reference： [1]Patent: US2014/155409,2014,A1 .Location in patent: Paragraph 0198; 0199; 0200; 0201; 0202; 0203
[2]Patent: US2015/297539,2015,A1 .Location in patent: Paragraph 0418-0422

20
[ 1929-29-9 ]
[ 4654-08-4 ]