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Diosgenin

Diosgenin structure

Diosgenin 

structure
  • CAS No:

    512-04-9

  • Formula:

    C27H42O3

  • Chemical Name:

    Diosgenin

  • 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

  • Categories:

    Biochemical Engineering  >  Plant Extracts

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.

Diosgenin Basic Attributes

414.62100

414.62

208-134-3

K49P2K8WLX

2932999099

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.

Drug Information

Diosgenin

Diosgenin Use and Manufacturing

Uses

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

Downstream Products

Drug Function and Efficacy

Skin conditioning, anti-inflammatory, anti-sensitivity, antibacterial

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

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