(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-ol

• ChemBase ID: 72986
• Molecular Formular: C29H48O
• Molecular Mass: 412.69082
• Monoisotopic Mass: 412.37051616
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](/C=C/[C@@H](CC)C(C)C)C)C)O
• Canonical SMILES: CC[C@@H](C(C)C)/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C
• InChI: InChI=1S/C29H48O/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/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
• InChIKey: HCXVJBMSMIARIN-PHZDYDNGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol; (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
• IUPAC Traditional name: stigmasterol
• Synonyms: Stigmasterol; Stigmasterin; Beta-Stigmasterol; Stigmasterol; Stigmasta-5,22-dien-3-ol; (3β,22E)-Stigmasta-5,22-dien-3-ol; Stigmasta-5,22-dien-3β-ol; 24-Ethyl-5,22-cholestadien-3β-ol; 24β-Ethyl-5,22-cholestadien-3β-ol; NSC 8095; 3β-羟基-24-乙基-5,22-胆甾二烯; 5,22-豆甾二烯-3β-醇; 豆固醇; 豆甾醇

Database IDs

• CAS Number: 83-48-7
• EC Number: 201-482-7
• MDL Number: MFCD00003630
• Beilstein Number: 2568182
• PubChem SID: 24899523; 162037906
• PubChem CID: 5280794

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.482555
• LogD (pH = 7.4): 7.482555
• Log P: 7.482555
• Molar Refractivity: 130.8827 cm^3
• Polarizability: 51.43686 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Cryst.; White Solid
• Melting Point: 151-153°C; 165-167 °C(lit.)

Safety Information

• Storage Condition: -20°C; Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... POLA1(5422), TOP2A(7153)rat ... Polb(29240)

Product Information

• Purity: ~95%
• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2361

Research Area: Metabolic Disease
Biological Activity:
Stigmasterol(Stigmasterin) is used as a precursor in the manufacture of synthetic progesterone, a valuable human hormone that plays an important physiological role in the regulatory and tissue rebuilding mechanisms related to estrogen effects, as well as acting as an intermediate in the biosynthesis of androgens, estrogens, and corticoids. It is also used as the precursor of vitamin D3. Research has indicated that stigmasterol may be useful in prevention of certain cancers, including ovarian, prostate, breast, and colon cancers. [1]

Sigma Aldrich - S2424

包装
1 g in poly tube
5, 10, 25 g in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S2424.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - S686750

Plant sterol, used as a precursor in the synthesis of progesterone.

REFERENCES

• http://en.wikipedia.org/wiki/Stigmaste
• Han, P., et al.: Biotechnol. App. Biochem., 54, 105 (2009)
• Matsunaga, I., et al.: Anal. Biochem., 393, 222 (2009)
• Huang, C., et al.: Plant Physiol., 150, 1192 (2009)