512-04-9 Usage
Description
Diosgenin, a triterpene and glycone derivative of dioscin, is a naturally occurring steroidal sapogenol found in various plant sources such as yams, Trigonella foenum-graecum, and Costus speciosus. It is characterized by its white to off-white solid appearance and possesses significant biological activities, making it a valuable compound in the pharmaceutical and healthcare industries.
Uses
Used in Pharmaceutical Industry:
Diosgenin is used as a precursor for the synthesis of various steroidal drugs, including corticosteroids, sex hormones like estrogen and progesterone, and other steroidal medications. Its ability to be converted into these hormones makes it a crucial component in the production of medications for hormonal imbalances, contraceptives, and treatments for certain cancers.
Used in Anti-Inflammatory Applications:
Diosgenin is utilized as an anti-inflammatory agent, helping to reduce inflammation and alleviate pain associated with various conditions. Its anti-inflammatory properties make it a potential candidate for the development of new drugs to treat inflammation-related disorders.
Used in Hormone Regulation:
Diosgenin is used as a natural source of estrogen, which plays a vital role in the regulation of the menstrual cycle, pregnancy, and the development and maintenance of female sexual characteristics. It can be used in hormone replacement therapy for menopausal women and as a component in the treatment of various estrogen-related conditions.
Used in Cholesterol Management:
Diosgenin is used as a cholesterol-lowering agent, as it has been shown to lower plasma cholesterol levels by increasing fecal cholesterol excretion. This makes it a potential ingredient in dietary supplements and herbal medicines aimed at improving cardiovascular health.
Used in Food Supplements and Herbal Medicines:
Diosgenin is found in some food supplements and herbal medicines, where it contributes to various health benefits, including cholesterol management and anti-inflammatory effects. Its presence in these products highlights its versatility and potential for use in maintaining overall health and well-being.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 512-04-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 512-04:
(5*5)+(4*1)+(3*2)+(2*0)+(1*4)=39
39 % 10 = 9
So 512-04-9 is a valid CAS Registry Number.
512-04-9Relevant articles and documents
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Walens et al.
, p. 182,185 (1957)
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Gould et al.
, p. 3685,3687 (1952)
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Krider,Wall
, p. 2938 (1954)
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Bivalent furostene carbamates as antiproliferative and antiinflammatory agents
Pathak, Nandini,Fatima, Kaneez,Singh, Sneha,Mishra, Divya,Gupta, Amit Chand,Kumar, Yogesh,Chanda, Debabrata,Bawankule,Shanker, Karuna,Khan, Feroz,Gupta, Atul,Luqman, Suaib,Negi, Arvind S.
, (2019/09/03)
Breast cancer is the most prevalent cancer in women affecting about 12% of world's female population. It is a multifactorial disease, mostly invasive in nature. Diosgenin and related compounds are potent antiproliferative agents. Carbamate derivatives have been synthesized at C26 of furostene ring after opening spiroketal bond (F-ring) of diosgenin. Compound 10 possessed significant antiproliferative activity against human breast cancer cells by arresting the population at G1 phase of cell division cycle and induced apoptosis. Induction of apoptosis was observed through the caspase signalling cascade by activating caspase-3. Moreover, carbamate 10 exhibited moderate antiinflammatory activity by decreasing the expression of cytokines, TNF-α and IL-6 in LPS-induced inflammation in primary macrophage cells. Furthermore, compound 10 significantly reduced Ehrlich ascites carcinoma significantly in mice. It was well tolerated and safe in acute oral toxicity in Swiss albino mice. The concomitant anticancer and antiinflammatory properties of carbamate 10 are important and thus, can further be optimized for a better anti-breast cancer candidate.
From organocatalysed desilylations to high-yielding benzylidenations of electron-deficient benzaldehydes
Niu, Qun,Xing, Linlin,Li, Chunbao
, p. 358 - 364 (2017/06/19)
A new type of organoprecatalyst (MeSCH2Cl/KI) for desilylation and benzylidenation reactions has been designed. Both reactions are user friendly and high yielding (71->99%) and have fast reaction rates. The desilylation of iodo silyl ethers was achieved with no sequential etherification side reactions like those seen for reactions when using TBAF. In the application of the catalytic system to a 6-TBDMS ether of a glucoside, glucoside benzylidenations using electron-deficient benzaldehydes were achieved in 87% yield compared with the previously reported yields of 69-77%. Altogether, 14 benzylidenation reactions were realised using silyloxy alcohols and electrondeficient benzaldehydes instead of their activated acetal forms. In terms of reaction rates and yields, the order of the benzylidenations is p-fluorobenzaldehyde > benzaldehyde > p-anisaldehyde, and a possible mechanism is discussed. These experiments have preliminarily differentiated this cost-effective catalytic system from the classic Lewis acids.
Electrochemical synthesis of glycoconjugates from activated sterol derivatives
Tomkiel, Aneta M.,Kowalski, Jan,P?oszyńska, Jolanta,Siergiejczyk, Leszek,?otowski, Zenon,Sobkowiak, Andrzej,Morzycki, Jacek W.
, p. 60 - 67 (2014/03/21)
Several derivatives of cholesterol and other 3β-hydroxy- Δ5-steroids were prepared and tested as sterol donors in electrochemical reactions with sugar alcohols. The reactions afforded glycoconjugates with sugar linked to a steroid moiety by an ether bond. Readily available sterol diphenylphosphates yielding up to 54% of the desired glycoconjugate were found to be the best sterol donors.