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Chemistry

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Also known as: 83-46-5, Sitosterol, Cupreol, Azuprostat, 22,23-dihydrostigmasterol, Quebrachol

Molecular Formula

C₂₉H₅₀O

Molecular Weight

414.7 g/mol

InChI Key

KZJWDPNRJALLNS-VJSFXXLFSA-N

FDA UNII

S347WMO6M4

sitosterol is a natural product found in Elodea canadensis, Ophiopogon intermedius, and other organisms with data available.

1 2D Structure

Soybean oil sterols phytosterols

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

2.1.2 InChI

InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

2.1.3 InChI Key

KZJWDPNRJALLNS-VJSFXXLFSA-N

2.1.4 Canonical SMILES

CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C

2.1.5 Isomeric SMILES

CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C

2.2 Other Identifiers

2.2.1 UNII

S347WMO6M4

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 24-ethylcholest-5-en-3 Beta-ol

2. 24-ethylcholesterol

3. 3beta-sitosterol

4. 3beta-stigmast-5-en-3-ol

5. Clionasterol

6. Gamma-sitosterol

7. Harzol

8. Sitosterol

9. Sitosterol, (3beta)-isomer

10. Sitosterol, (3beta,24xi)-isomer

11. Sitosterol, 26-(14)c-labeled

12. Stigmast-5-en-3-ol, (3beta,24s)-

2.3.2 Depositor-Supplied Synonyms

1. 83-46-5

2. Sitosterol

3. Cupreol

4. Azuprostat

5. 22,23-dihydrostigmasterol

6. Quebrachol

7. Triastonal

8. Cinchol

9. Harzol

10. Rhamnol

11. Beta-sitosterin

12. Nimbosterol

13. B-sitosterol

14. (-)-beta-sitosterol

15. Alpha-dihydrofucosterol

16. Prostasal

17. Sito-lande

18. 24alpha-ethylcholesterol

19. (24r)-ethylcholest-5-en-3beta-ol

20. (3beta)-stigmast-5-en-3-ol

21. Betaprost

22. Sobatum

23. Beta Sitosterol

24. Alpha-phytosterol

25. (24r)-stigmast-5-en-3beta-ol

26. Angelicin (steroid)

27. Skf 14463

28. Beta-sistosterol

29. Stigmast-5-en-3beta-ol

30. A-dihydrofucosterol

31. Phytosterol

32. Chebi:27693

33. Nsc8096

34. Sitosterol, Beta

35. Stigmast-5-en-3-ol, (3beta)-

36. .alpha.-dihydrofucosterol

37. Chembl221542

38. S347wmo6m4

39. .beta.-sitosterol

40. Nsc-8096

41. Nsc49083

42. .alpha.-phytosterol

43. Sitosterol, .beta.

44. Nsc 18173

45. Nsc-18173

46. Nsc-49083

47. Stigmasterol,23-dihydro-

48. Steroids, Hydroxy

49. Stigmasterol, 22,23-dihydro-

50. Sitosterin

51. .beta.-sitosterin

52. Nsc 8096

53. Sitosterol, Beta-

54. Stigmast-5-en-3-ol, (3.beta.)-

55. (3s,8s,9s,10r,13r,14s,17r)-17-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol

56. 24.alpha.-ethylcholesterol

57. Stigmast-5-en-3-ol, (3b)-

58. Stigmast-5-en-3.beta.-ol

59. Sr-05000002307

60. 24-alpha-ethylcholesterol

61. Stigmast-5-en-3-beta-ol

62. Unii-s347wmo6m4

63. Delta5-stigmasten-3-beta-ol

64. Sitosterol Beta

65. A-phytosterol

66. B-sitosterin

67. Beta-phytosterol

68. Ccris 5529

69. Ss--sitosterol

70. .beta.sitosterin

71. .beta.sitosterol

72. Beta -sitosterol

73. (3-beta)-stigmast-5-en-3-ol

74. Cas-83-46-5

75. Ncgc00095716-01

76. (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-ol

77. (3s,8s,9s,10r,13r,14s,17r)-17-[(1r,4r)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol

78. Einecs 201-480-6

79. (-)-b-sitosterol

80. Harzol (tn)

81. Mfcd00003631

82. 24a-ethylcholesterol

83. Alpha.dihydrofucosterol

84. D5-stigmasten-3b-ol

85. Stigmast-5-en-3b-ol

86. Ai3-26020

87. Prestwick0_000985

88. Prestwick1_000985

89. Prestwick2_000985

90. Prestwick3_000985

91. Delta5-stigmasten-3b-ol

92. Stigmast-5-ene-3beta-ol

93. Dsstox_cid_2481

94. Beta-sitosterol, >=70%

95. Sitosterol [mart.]

96. Beta-sitosterol (synthetic)

97. Dsstox_rid_76601

98. Sitosterol [who-dd]

99. Bidd:pxr0121

100. Dsstox_gsid_22481

101. Schembl16105

102. 22,23-dihydro-stigmasterol

103. Bspbio_001049

104. Bidd:er0636

105. Spbio_002950

106. Beta-sitosterol [inci]

107. Bpbio1_001155

108. Megxp0_001710

109. Beta Sitosterol [vandf]

110. .beta.-sitosterol [mi]

111. Dtxsid5022481

112. (24r)-stigmast-5-en-3b-ol

113. Acon1_000287

114. Beta-sitosterol [usp-rs]

115. Chebi:176889

116. Hms1571e11

117. Hms2098e11

118. (24r)-ethylcholest-5-en-3b-ol

119. 24-ethylcholest-5-en-3.beta.-ol

120. Nsc18173

121. Zinc4095717

122. Beta-sitosterol, Analytical Standard

123. Tox21_111514

124. Bdbm50218197

125. Beta-sitosterol, Synthetic, >=95%

126. Lmst01040129

127. S2273

128. Akos005267194

129. Ccg-208334

130. Db14038

131. Beta-sitosterol, From Soybean, >=96%

132. Smp1_000274

133. Ncgc00142598-02

134. Ncgc00142598-03

135. (3.beta.)-stigmast-5-en-3-ol

136. 14-((1s,4r)-4-ethyl-1,5-dimethylhexyl)(1s,5s,10s,11s,2r,14r,15r)-2,15-dimethyl Tetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-7-en-5-ol

137. Ac-24183

138. Nci60_041777

139. Ab00513984

140. N1688

141. S0040

142. .delta.(sup 5)-stigmasten-3.beta.-ol

143. C01753

144. D08518

145. A840577

146. Alpha-dihydrofucosterol, 22,23-dihydrostigmasterol

147. Q-200712

148. Sr-05000002307-2

149. Sr-05000002307-3

150. Q63409374

151. .beta.-sitosterol (constituent Of Pygeum) [dsc]

152. Beta-sitosterol (constituent Of Saw Palmetto) [dsc]

153. Beta-sitosterol, Analytical Standard, From Soybean, >=40%

154. Beta-sitosterol, Primary Pharmaceutical Reference Standard

155. 24.beta.-ethyl-.delta.(sup 5)-cholesten-3.beta.-ol

156. Beta-sitosterol (constituent Of Stinging Nettle) [dsc]

157. Beta-sitosterol, European Pharmacopoeia (ep) Reference Standard

158. Beta-sitosterol, United States Pharmacopeia (usp) Reference Standard

159. Beta-sitosterol, Certified Reference Material, 100 Mug/ml In Chloroform

160. (3s,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-ol

161. .beta.-sitosterol (constituent Of Echinacea Angustifolia Root, Echinacea Pallida Root, Echinacea Purpurea Root And Echinacea Purpurea Aerial Parts) [dsc]

162. 17-(5-ethyl-6-methyl-heptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol

163. 76772-70-8

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₅₀O
Molecular Weight	414.7 g/mol
XLogP3	9.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	6
Exact Mass	414.386166214 g/mol
Monoisotopic Mass	414.386166214 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	634
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Hypolipidemic Agents

Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS. (See all compounds classified as Hypolipidemic Agents.)

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