Diosgenin

ChemicalBook > CAS DataBase List > Diosgenin

Product Name: Diosgenin
CAS No.: 512-04-9
Chemical Name: Diosgenin
Synonyms: SAPOGENIN;diosgen;DIOSGENIN (3B-HYDROXY-5A-SPIROSCENE);6-Keto Diosgenin;3β-Hydroxy-5-spirostene;SP 37;Diosg;C08898;iosgenin;Diosgemom
CBNumber: CB2685481
Molecular Formula: C27H42O3
Formula Weight: 414.63
MOL File: 512-04-9.mol

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Diosgenin Property

Melting point:: 205-208°C
alpha: D25 -129° (c = 1.4 in CHCl3)
Boiling point:: 473.46°C (rough estimate)
Density: 1.0483 (rough estimate)
refractive index: 1.4700 (estimate)
storage temp.: 2-8°C
solubility: chloroform: 20 mg/mL, clear, slightly yellow
pka: 15.02±0.70(Predicted)
form: Solid
color: White to Pale Yellow
Water Solubility: Soluble in chloroform (50 mg/ml), ethanol (83 mg/ml at 25°C), water (<1 mg/ml at 25°C), DMSO (<1 mg/ml at 25°C), and methanol.
Merck: 14,3295
BRN: 94582
LogP: 6.602 (est)
CAS DataBase Reference: 512-04-9(CAS DataBase Reference)
NIST Chemistry Reference: Diosgenin(512-04-9)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36/37-24/25
WGK Germany: 2
RTECS: WH1450000
HS Code: 29329990

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: D1634
Product name: Diosgenin
Purity: ≥93%
Packaging: 5g
Price: $68.2
Updated: 2024/03/01

Sigma-Aldrich

Product number: D1634
Product name: Diosgenin
Purity: ≥93%
Packaging: 100g
Price: $453
Updated: 2024/03/01

Sigma-Aldrich

Product number: Y0001871
Product name: Diosgenin
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: Y0001871
Price: $149
Updated: 2023/06/20

TCI Chemical

Product number: D1474
Product name: Diosgenin
Purity: >95.0%(GC)
Packaging: 1g
Price: $23
Updated: 2024/03/01

TCI Chemical

Product number: D1474
Product name: Diosgenin
Purity: >95.0%(GC)
Packaging: 10g
Price: $104
Updated: 2024/03/01

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Diosgenin Chemical Properties,Usage,Production

Chemical Properties

White to Off-White Dolid

Occurrence

Primary sources of diosgenin (a steroidal sapogenin) include Smilax China, Rhizoma polygonati, Solanum incanum, Solanum xanthocarpum, Dioscorea villosa, Trigonella foenum graecum (fenugreek), and Dioscorea Linn (wild yams). It is commercially obtained from wild yam tubers and rootstock[1-2].

Uses

antiinflammatory, estrogen

Uses

Aglicone of saponin dioscin. Diosgenin exists in some food supplements and herbal medicines and lowers plasma cholesterol by increasing fecal cholesterol excretion. e and Progesterone.

Uses

pregnenolone and progesterone precursor

Definition

ChEBI: 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.

benefits

A steroidal saponin, diosgenin, and its chemical and structural variants are helpful in treating a great variety of chronic conditions, including cardiovascular disease, several forms of lethal malignancies, nervous system problems, and autoimmune diseases. Diosgenin is considered an essential precursor of steroidal drugs. Diosgenin is gaining enormous attention over regular synthetic drugs among researchers and industry people throughout the world due to its beneficial effect on chronic illnesses such as high levels of cholesterol, stroke, diabetes, tumor, Alzheimer, inflammation, leukaemia, climacteric syndrome, depression, thrombosis and even cancer and other various metabolic diseases. Diosgenin has been shown to act on several molecular targets that are essential players in the occurrence and incidence of many serious disorders. Its multitargeting capability allows it to influence multiple molecular targets and signaling pathways at the same time[1-2].

General Description

Diosgenin is a triterpene and a glycone derivative of dioscin. Yams, Trigonella foenum-graecum and Costus speciosus are some of its source.

Biochem/physiol Actions

Diosgenin induces apoptosis in colon cancer cell lines and induces apoptosis, cell cycle arrest and cyclooxygenase activity in osteosarcoma cells. It serves as a precursor in steroid drug production. Diosgenin is shown to promote cholesterol production by stimulating biliary excretion. It influences lipoxygenase induced human erythroleukemia cell line differentiation.

Anticancer Research

It is a steroidal saponin and legumes and yams are the rich sources of it. It is a notoriousprecursor of several synthetic steroidal drugs. It suppresses growth of cells andinduces apoptosis in human osteosarcoma, colon cancer, and leukemia. Its anticancermechanism is by arresting the cell cycle, disrupting the calcium homeostasis,activating p53, releasing apoptosis inducing factors, and modulating caspase-3activity. It suppresses NF-κB activation induced by TNF as a result of DNA binding,IκBα kinase activation, degradation, phosphorylation, p65 nuclear translocation,and phosphorylation. It suppresses proliferation and invasion and induces apoptosisby downregulation of cFLIP, cyclin-D1, TRAF1, COX-2, c-myc, Bfl-1/A1, BclxL,IAP1, Bcl-2, and MMP-9 (Aggarwal et al. 2008; Raju and Mehta 2008).

Purification Methods

Crystallise diosgenin from acetone, and chromatograph it on Al2O3 and elute with *C6H6/Et2O (9:1), then recrystallise it from MeOH. Its solubility is ~4% in H2O and 5% in CHCl3. The acetate crystallises from AcOH with m 198o; and has [] D 20 -119o (pyridine). [Marker et al. J Am Chem Soc 65 1199 1943. Mazur et al. J Am Chem Soc 82 5889 1960, Beilstein 19 IV 862.]

References

[1] Prajya Arya , Pradyuman Kumar, Mohona Munshi . “Diosgenin: Chemistry, extraction, quantification and health benefits.” Food chemistry advances 2 (2023): Article 100170.
[2] Mafalda Jesus. “Diosgenin: Recent Highlights on Pharmacology and Analytical Methodology.” Journal of Analytical Methods in Chemistry 45 1 (2016).

Diosgenin Preparation Products And Raw materials

Raw materials

Turmeric

Preparation Products

11a-Hydroxy-16,17a-epoxyprogesterone 17α-Hydroxyprogesterone 16,17-Epoxypregnenolone 16,17-Epoxypregn-4-ene-3,11,20-trione 16-Dehydropregnenolone acetate 21-DEOXYCORTISONE 17-Hydroxy-21-iodoprogesterone 16-Bromo-17-hydroxypregn-4-en-3,20-dione 16a,17a-Epoxyprogesterone REICHSTEIN'S SUBSTANCE S 21-ACETATE

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View Lastest Price from Diosgenin manufacturers

Hebei Dangtong Import and export Co LTD

Product: Diosgenin 512-04-9
Price: US $68.00-50.00/g
Min. Order: 1g
Purity: 99%
Supply Ability: 5000g
Release date: 2023-09-15

Shaanxi Cuikang Pharmaceutical Technology Co., Ltd

Product: Diosgenin 512-04-9
Price: US $0.00/kg
Min. Order: 1kg
Purity: HPLC≥98%
Supply Ability: 1000kg
Release date: 2024-03-14

Hebei Kingfiner Technology Development Co.Ltd

Product: Diosgenin 512-04-9
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 50000kg
Release date: 2024-05-30

512-04-9, DiosgeninRelated Search:

methyl protodioscin TRIBULOSIDE Sarsasapogenin Escin Dioscin CHLOROPHOSPHONAZO III Tigogenin Saponin D-(-)-Salicin Neosperidin dihydrochalcone Icariin Wild Yam Extract RUSCOGENIN Diosgenin 3-glucoside ophiopogonin B Ophiopogonin A Protodioscin OPHIOPOGONIN C

Diosgemom

DIOCTYLMALONATE

DIOSGENIN (3B-HYDROXY-5A-SPIROSCENE)

20F,22F-Spirosten-3-ol

22alpha-Spirost-5-en-3beta-ol

25d-Spirost-5-en-3b-ol

5-22-Spirosten-3-ol

5-25D-Spirosten-3-ol

delta 5,20a,22a,25D-spirosten-3beta-ol

Nitrogenin

SP 37

Spiro(8H-naphth(2',1':4,5)-indeno(2,1-b)furan-8,2'-(2H)-pyran)-2-ol, 1,2,3,3',4,4',4a,4b,5,5',6,6',6a,6b,7,9a,10,10a,10b,11-eicosahydro-4a,5',6a,7-tetramethyl-

Spiro[8H-naphth[2',1':4,5]indeno[2,1-b]furan-8,2'-[2H]pyran],

Spiro[8H-naphth[2',1':4,5]indeno[2,1-b]furan-8,2'-[2H]pyran], spirost-5-en-3-ol deriv.

Spirost-5-en-3beta-ol, (25R)-

Spirost-5-en-3b-ol, (25R)-

Spirost-5-en-3-ol

(25R)-5-Spirosten-3β-ol, 3β-Hydroxy-5-spirostene

(25R)-5-Spirosten-3b-ol

(25R)-3β-Hydroxyspirosta-5-ene

3β-Hydroxy-5-spirostene

Diosgenin,(25R)-5-Spirosten-3β-ol, 3β-Hydroxy-5-spirostene

(3β,25R)-

Dioscorea sapogenin

5,7',9',13'-tetraMethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-ol

Spirost-5-en-3-ol, (3β,25R)-

Diosgenin (25R)-Spirost-5-en-3beta-ol

diosgen

DIOSGENIN

HYDROXY-5-SPIROSTENE

3b-hydroxy-5-spirostene

3BETA-HYDROXY-5-SPIROSTENE

5,25R-SPIROSTEN-3BETA-OL

Diosgenin 512-04-9

5,20-ALPHA, 22-ALPHA, 25D-SPIROSTEN-3-BETA-OL

5, 20, 22, 25D-SPIROSTEN-3-OL

[25R]-5-SPIROSTEN-3BETA-OL

(25R)-Spirost-5-en-3beta-ol

NITOGENIN

SAPOGENIN

(25r)-spirost-5-en-3-beta-o

(25R)-Spirost-5-en-3b-ol

(25R)-Spirost-5-en-3-ol

(20R,25R)-spirost-5-en-3-beta-ol

Diosgenin,95%

DIOSGENIN & DERIVATIVES

Wild Yam Extract/Diosgenin

(3.beta.,25R)-Spirost-5-en-3-ol

(3-beta,25r)-spirost-5-en-3-o

Spirost-5-en-3-ol deriv.

Spirost-5-en-3-ol, (3b,25R)-

Spirost-5-en-3-ol, (3beta,25R)-

6-Keto Diosgenin

(25R)-5-Spirostene-3-beta-ol

Diosgenin=Nitogenin

(25r)-5-spirosten-3β-ol

C08898

DIOSGENIN(SAPOGENIN)(P)