54522-52-0

Basic information

• Product Name: methyl protodioscin
• Synonyms: methyl protodioscin;[(22R,25R)-22-Methoxy-26-(β-D-glucopyranosyloxy)furosta-5-ene-3β-yl]2-O,4-O-di-α-L-rhamnopyranosyl-β-D-glucopyranoside;[(25R)-26-(β-D-Glucopyranosyloxy)-22α-methoxyfurost-5-en-3β-yl]2-O,4-O-bis(α-L-rhamnopyranosyl)-β-D-glucopyranoside;3b,26-Dihydroxy-22a-methoxyfurost-5-ene 3-O-beta-chacotrioside 26-O-beta-D-glucopyranoside;Smilax saponin B;Methylprotodioscin(SMilax saponin B);22-Methoxylprotodioscin;22-O-Methylprotodioscin
• CAS NO: 54522-52-0
• Molecular Formula: C₅₂H₈₆O₂₂
• Molecular Weight: 1063.23
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 54522-52-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 175-177 °C
• Appearance: /
• Density: 1.43
• Refractive Index: 1.619
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Pyridine (Slightly), Water (Slightly)
• PKA: 12?+-.0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: methyl protodioscin(CAS DataBase Reference)
• NIST Chemistry Reference: methyl protodioscin(54522-52-0)
• EPA Substance Registry System: methyl protodioscin(54522-52-0)

Safety Data

• Hazardous Substances Data: 54522-52-0(Hazardous Substances Data)

Usage

Description

Methyl protodioscin is a steroidal saponin compound derived from various plant species, predominantly recognized as the active component of the herbal aphrodisiac plant Tribulus terrestris. This bioactive molecule has demonstrated the ability to significantly increase hormonal levels in animal studies, showcasing its potential in the realm of pharmaceuticals and supplements.

Uses

Used in Pharmaceutical Applications:
Methyl protodioscin is used as a pharmaceutical agent for its hormone-boosting properties. It has been found to elevate hormonal levels in animal studies, which may have implications for treating hormonal imbalances or enhancing overall health and well-being.
Used in Herbal Aphrodisiacs:
In the herbal aphrodisiac industry, methyl protodioscin is used as an active ingredient for its potential to enhance libido and sexual performance. As a component of Tribulus terrestris, it is believed to contribute to the plant's reputation as a natural aphrodisiac and may be utilized in the development of supplements and remedies aimed at improving sexual function.
Used in Hormonal Regulation:
Methyl protodioscin is used as a hormonal regulator, particularly for individuals experiencing hormonal imbalances or those seeking to improve their overall hormonal health. Its demonstrated ability to increase hormonal levels in animal studies suggests that it may play a role in maintaining or restoring hormonal balance in humans.
Used in Sports Nutrition:
In the sports nutrition industry, methyl protodioscin is used as a performance-enhancing supplement. Its hormone-boosting properties may help athletes improve their physical performance, muscle growth, and recovery, making it a valuable addition to pre-workout and training regimens.
Used in Research and Development:
Methyl protodioscin is also used as a subject of research and development in the biotechnology and pharmaceutical sectors. Its potential applications in hormone regulation, aphrodisiac effects, and sports nutrition make it an interesting compound for further study and potential product development.

InChI:InChI=1/C52H86O22/c1-21(20-66-46-40(61)39(60)36(57)31(18-53)70-46)10-15-52(65-7)22(2)33-30(74-52)17-29-27-9-8-25-16-26(11-13-50(25,5)28(27)12-14-51(29,33)6)69-49-45(73-48-42(63)38(59)35(56)24(4)68-48)43(64)44(32(19-54)71-49)72-47-41(62)37(58)34(55)23(3)67-47/h8,21-24,26-49,53-64H,9-20H2,1-7H3/t21-,22+,23+,24+,26+,27-,28+,29+,30+,31-,32-,33+,34+,35+,36-,37-,38-,39+,40-,41-,42-,43+,44-,45?,46-,47+,48+,49-,50+,51+,52-/m1/s1

Upstream product

• 67-56-1 methanol 

Downstream Products

• 67-56-1 methanol 
• 6014-42-2 L-rhamnose 
• 78229-03-5 26-O-β-D-Glucopyranosylpseudodiosgenin-3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosid 
• 18615-48-0 L-arabino-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 534-97-4 glucosazone 
• 109606-09-9 kryptogenin 3-O-β-chacotrioside 
• 21494-98-4 trigonelloside C 
• 19057-60-4 3-O-{α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl}-25(S)-spirost-5-en-3β-ol 
• 21494-98-4 proto-dioscin 
• 2280-44-6 D-Glucose 
• 19057-60-4 (25S)spirost-5-en-3β-ol-3-O-<α-L-rhamnopyranosyl(1-2)> <α-L-rhamnopyranosyl(1-4)>-β-D-glucopyranoside 
• 470-05-3 diosgenin 
• 73-34-7 L-rhamnose 
• 109617-40-5 3-O-β-chacotriosyl kryptogenin 26-O-β-D-glucoside 

Relevant articles and documents

Antineoplastic agents; II. Four furostanol glycosides from rhizomes of Dioscorea collettii var. hypoglauca

During activity-guided fractionations to screen for antineoplastic agents, further studies by means of preparative HPLC led to the isolation of four known furostanol saponins: protoneodioscin, protodioscin, protoneogracillin, protogracillin, along with their corresponding artifacts: methyl protoneodioscin, methyl protodioscin, methyl protoneogracillin, and methyl protogracillin, from the rhizomes of Dioscorea collettii var. hypoglauca. Among them, protoneodioscin, protodioscin, and protoneogracillin are first reported from the title plant. The structures of the compounds were established on the basis of chemical evidence and spectral analysis (1H-NMR, 13C-NMR, 1H-1H COSY, HMQC, HMBC, and FAB-MS). These eight compounds all caused morphological abnormality of Pyricularia oryzae mycelia. They also showed cytotoxic activities against the cancer cell line of K562 in vitro as antineoplastic agents.