[ CAS No. 474-58-8 ] {[proInfo.proName]}

Name: 474-58-8|(2R,3R,4S,5S,6R)-2-(((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol|98%
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SKU: A314174
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Quality Control of [ 474-58-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 474-58-8 ]

SDS Specification

Alternatived Products of [ 474-58-8 ]

Product Details of [ 474-58-8 ]

CAS No. :	474-58-8	MDL No. :	MFCD01683621
Formula :	C₃₅H₆₀O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NPJICTMALKLTFW-OFUAXYCQSA-N
M.W :	576.85	Pubchem ID :	5742590
Synonyms :	Eleutheroside A;β-Sitosterol β-D-glucoside;Lyoniside, Daucosterol, Eleutheroside A, Alexandrin, Coriandrinol, Daucosterin, beta-Sitosterol glucoside, β-Sitosterol-D-glucoside;NSC 165962;Sitogluside	Chemical Name :	(2R,3R,4S,5S,6R)-2-(((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Calculated chemistry of [ 474-58-8 ]

Physicochemical Properties

Num. heavy atoms :	41
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.94
Num. rotatable bonds :	9
Num. H-bond acceptors :	6.0
Num. H-bond donors :	4.0
Molar Refractivity :	165.61
TPSA :	99.38 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	5.17
Log Po/w (XLOGP3) :	7.74
Log Po/w (WLOGP) :	5.85
Log Po/w (MLOGP) :	3.96
Log Po/w (SILICOS-IT) :	5.02
Consensus Log Po/w :	5.55

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-7.7
Solubility :	0.0000115 mg/ml ; 0.00000002 mol/l
Class :	Poorly soluble
Log S (Ali) :	-9.67
Solubility :	0.000000123 mg/ml ; 0.0000000002 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-4.4
Solubility :	0.0228 mg/ml ; 0.0000394 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	8.02

Safety of [ 474-58-8 ]

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 [ 474-58-8 ]

* 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 [ 474-58-8 ]
Downstream synthetic route of [ 474-58-8 ]

[ 474-58-8 ] Synthesis Path-Upstream 1~19

1
[ 2280-44-6 ]
[ 83-46-5 ]
[ 474-58-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With trimethylsilyl trifluoromethanesulfonate In ethylbenzene at 85℃; for 15 h;	β-sitosterol124.4g0.3mol),D-glucose (18.0 g, 0.1 mol) dissolved in ethylbenzene (600 mL).At 80°C,TMSOTf (8.9 g/7.3 mL, 40 mmol)was added and underprotection carried out constant temperature reaction until the TLC detected almost complete disappearance of D-glucose (about 15h). After the reaction was concentrated , it wassubjected to silica gel column chromatography (silica gel 100-200 mesh) using dichlromethaneas eluent. TLC assay until the eluent is free of β-sitosterol, the eluent was concentrated to give β-sitosterol(83.0g, 0.2mol), continue the elution with ethyl acetateas eluent, and TLC assay until there is no title compoundin the eluent. The eluent was concentrated to give the title compound (47.3 g) in 82percent yield and HPLC purity 97.8percent.

Reference： [1] Patent: CN104693266, 2018, B, . Location in patent: Paragraph 0062-0064

2
[ 4282-00-2 ]
[ 474-58-8 ]

Yield	Reaction Conditions	Operation in experiment
41%	for 24 h; Inert atmosphere	β-sitosteryl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1.3×10−3 mmol) was added to a 100 ml round bottom flask which was under nitrogen atmosphere, 15percent sodium methoxide(20.00 ml) was added to it and stirred 24 h. After completion of the reaction, mixture was quenched with 1 g of ice. The white residue obtained was recrystallized from acetone. Yield was 41percent. IR spectrum showed absorption peaks in the regions of 3600–3400 cm⁻¹(-OHgroup), 2900–2850 cm⁻¹ (aliphatic asymmetric C-H stretching), 900 cm⁻¹(out of plane C-H bending), 830–800 cm⁻¹( -C=C-H stretching).

Reference： [1] Journal of Pharmaceutical Sciences, 1985, vol. 74, # 12, p. 1259 - 1264
[2] Molecular Crystals and Liquid Crystals, 2015, vol. 613, # 1, p. 94 - 102
[3] Soft Matter, 2012, vol. 8, # 1, p. 149 - 155

3
[ 137909-13-8 ]
[ 474-58-8 ]

Reference： [1] Phytochemistry (Elsevier), 1991, vol. 30, # 9, p. 2927 - 2931

4
[ 83-46-5 ]
[ 572-09-8 ]
[ 474-58-8 ]

Reference： [1] Journal of the Chemical Society, 1913, vol. 103, p. 1022,1026
[2] Journal of Organic Chemistry, 1953, vol. 18, p. 1473,1476
[3] Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 3273 - 3278
[4] Journal of Natural Products, 2001, vol. 64, # 7, p. 993 - 996

5
[ 83-46-5 ]
[ 474-58-8 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1985, vol. 74, # 12, p. 1259 - 1264
[2] Phytochemistry (Elsevier), 1991, vol. 30, # 9, p. 2927 - 2931

6
[ 1192023-60-1 ]
[ 474-58-8 ]
[ 60-33-3 ]

Reference： [1] Chemistry of Natural Compounds, 2009, vol. 45, # 3, p. 371 - 373

7
[ 572-09-8 ]
[ 474-58-8 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1985, vol. 74, # 12, p. 1259 - 1264

8
[ 4291-69-4 ]
[ 474-58-8 ]

Reference： [1] Phytochemistry (Elsevier), 1991, vol. 30, # 9, p. 2927 - 2931

9
[ 74808-09-6 ]
[ 474-58-8 ]

Reference： [1] Phytochemistry (Elsevier), 1991, vol. 30, # 9, p. 2927 - 2931

10
[ 53657-30-0 ]
[ 474-58-8 ]
[ 112-61-8 ]

Reference： [1] Phytochemistry (Elsevier), 1988, vol. 27, # 6, p. 1895 - 1896

11
[ 53657-29-7 ]
[ 474-58-8 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1984, # 4, p. 965 - 975

12
[ 18749-71-8 ]
[ 474-58-8 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1984, # 4, p. 965 - 975

13
[ 50-99-7 ]
[ 474-58-8 ]