Diosgenin
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Diosgenin
structure -
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CAS No:
512-04-9
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Formula:
C27H42O3
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Chemical Name:
Diosgenin
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Synonyms:
Spirost-5-en-3-ol,(3β,25R)-;Spirost-5-en-3β-ol,(25R)-;25D-Spirost-5-en-3β-ol;Spiro[8H-naphth[2′,1′:4,5]indeno[2,1-b]furan-8,2′-[2H]pyran],spirost-5-en-3-ol deriv.;(3β,25R)-Spirost-5-en-3-ol;Diosgenin;Nitogenin;(25R)-Spirost-5-en-3β-ol;25α-Spirost-5-en-3β-ol;NSC 33396
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CAS No:
Description
Diosgenin, a steroidal saponin, can inhibit STAT3 signaling pathway.
Diosgenin is a sapogenin that is spirostan which is substituted by a hydroxy group at the 3beta position, contains a double bond at the 5-6 position, and has R- configuration at position 25. A natural product found in Dioscorea (wild yam) species, it is used as the starting point for the commercial synthesis of a number of steroids, including cortisone, pregnenolone and progesterone. It has a role as an apoptosis inducer, an antiviral agent, an antineoplastic agent and a metabolite. It is a 3beta-sterol, a spiroketal, a hexacyclic triterpenoid and a sapogenin. It derives from a hydride of a spirostan.|A spirostan found in DIOSCOREA and other plants. The 25S isomer is called yamogenin. Solasodine is a natural derivative formed by replacing the spiro-ring with a nitrogen, which can rearrange to SOLANINE.
Characteristics
38.69000
5.71390
Flaky or needle crystal
1.13 g/cm3
205.5 °C
527.1ºC at 760 mmHg
272.6ºC
1.564
chloroform: 20 mg/mL, clear, slightly yellow
Refrigerator
208.4 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Safety Information
NONH for all modes of transport
2
R36/37/38
S26; S36/37
WH1450000
Xi
Stable at normal temperatures and pressures.
Diosgenin Use and Manufacturing
Can be converted to pregnenolone and progesterone.
Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Spirostanols and derivatives [ST0108]
Computed Properties
Molecular Weight:414.6
XLogP3:5.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:414.31339520
Monoisotopic Mass:414.31339520
Topological Polar Surface Area:38.7
Heavy Atom Count:30
Complexity:746
Defined Atom Stereocenter Count:11
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Skin conditioning, anti-inflammatory, anti-sensitivity, antibacterial
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