78574-94-4

Basic information

• Product Name: CYCLOASTRAGENOL
• Synonyms: (3beta,6alpha,16beta,20R,24S) 20,24-Epoxy-9,19-cyclolanostane-3,6,16,25-tetrol;Astramembrangenin;Cyclosieversigenin;CYCLOASTRAGENOL(SH);Cyclogalegenol;Cycloastragenol, 98%, from Astragalus membranaceus Bunge
• CAS NO: 78574-94-4
• Molecular Formula: C₃₀H₅₀O₅
• Molecular Weight: 490.72
• Mol File: 78574-94-4.mol
• Article Data: 31

Chemical Properties

• Melting Point: 241.0 to 245.0 °C
• Boiling Point: 617.174 °C at 760 mmHg
• Flash Point: 327.055 °C
• Appearance: /
• Density: 1.2 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.57±0.29(Predicted)
• CAS DataBase Reference: CYCLOASTRAGENOL(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOASTRAGENOL(78574-94-4)
• EPA Substance Registry System: CYCLOASTRAGENOL(78574-94-4)

Safety Data

• RTECS: GX8265000
• Hazardous Substances Data: 78574-94-4(Hazardous Substances Data)

Usage

Uses

Used in Dietary Supplements:
Cycloastragenol is used as a dietary supplement for its potential anti-aging properties, as it is believed to activate telomerase, an enzyme that protects and may extend telomeres, thus contributing to cellular health and longevity.
Used in Health and Wellness Products:
Cycloastragenol is used as an ingredient in health and wellness products, marketed to enhance immune function and promote overall health, capitalizing on its potential to activate telomerase and support cellular longevity.
Used in Research and Development:
Cycloastrogenol is used in scientific research and development, as scientists explore its potential applications in anti-aging and health-related fields, with a focus on understanding its effects on telomerase activity and cellular health.
Used in Pharmaceutical Industry:
Cycloastragenol is used as a potential therapeutic agent in the pharmaceutical industry, with ongoing studies aimed at determining its effectiveness in treating age-related conditions and promoting cellular health.
Note: The uses mentioned above are based on the potential properties of Cycloastragenol as described in the provided materials. It is important to emphasize that more research is needed to establish its effectiveness and safety for these purposes.

Upstream product

• 83207-58-3 astragaloside IV 
• 101858-42-8 cyclosieversioside E 
• 83207-58-3 cyclosieversioside F 
• 86408-19-7 Cyclosiversigenin 3-O-2)-β-D-xylopyranoside> 
• 88192-83-0 cyclosiversioside H 
• 88192-84-1 askenoside B 
• 86408-17-5 askendoside D 
• 86850-51-3 Cyclosiversioside G 
• 148297-88-5 cycloaraloside D 
• 86541-80-2 cyclosieversigenin 3,6-diacetate 
• 84680-75-1 (3β,6α,16β,20R,24S)-3-[(2,3-di-O-acetyl-β-D-xylopyranosyl)oxy]-20,24-epoxy-16,25-dihydroxy-9,19-cyclolanostan-6-yl β-D-glucopyranoside 
• 84676-89-1 (3b,6a,16b,20R,24S)-3-((2-O-acetyl-beta-D-xylopyranosyl)oxy)-20,24-epoxy-16,25-dihydroxy-9,19-cyclolanostan-6-yl beta-D-glucopyranoside 
• 84687-47-8 acetylastragaloside I 
• 84687-44-5 astragaloside V 

Downstream Products

• 11026-01-0 20(S),24(R)-epoxylanost-9(11)-ene-3β,6α,16β,25-tetraol 
• 84687-42-3 astragaloside III 
• 1255151-96-2 2-(L)-amino-3-phenyl-propionic acid 6α,16β-dihydroxy-17-[5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydrofuran-2-yl]-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3α-yl ester hydrochloride 
• 1255152-17-0 2-(L)-amino-3-phenyl-propionic acid 3β,16β-dihydroxy-17-[5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-6α-yl ester hydrochloride 
• 1255152-16-9 C₄₄H₆₇NO₈ 
• 1255151-95-1 C₄₄H₆₇NO₈ 
• 1255151-99-5 C₃₇H₅₄O₆ 
• 86541-79-9 astragenol 

Relevant articles and documents

The use of two-phase acid hydrolysis method of preparing ring [...] (by machine translation)

The invention belongs to the field of pharmaceutical chemicals, in particular to the use of double-phase acid hydrolysis method of preparing ring [...], including astragaloside as raw materials, and the organic phase and the acid solution of the two-phase acid aqueous solution mixing, reaction, after-treatment, to obtain the ring [...]; wherein organic phase immiscible with water or slightly soluble, ring [...] in the organic phase is greater than the solubility of the aqueous phase. This invention utilizes the double-phase acid hydrolysis method for preparing ring [...], making acid is hydrolyzed to generate ring [...] distribution in the organic phase, thereby avoiding the ring [...] in violent acid aqueous phase into the shortcoming of the [...], effectively protect the stability of the ring [...], [...] greatly improves the yield of the ring, and the step is simple, low cost, and is suitable for industrial production; through the standstill, layered, extraction, silica gel column chromatography separation to obtain high-purity [...]. (by machine translation)

Compositions and methods for skin conditioning

Methods and cosmetic compositions for conditioning the skin, utilizing as active ingredients selected compounds structurally related to astragenols, cycloastragenols, and/or protopanaxatriols, are provided. Such compounds include those of formulas (I), (II) and (III) described herein.

Triterpene glycosides from astragalus. Structure of cyclolehmanoside C from A. lehmannianus

The structure of a new cycloartane triterpene glycoside, cyclolehmanoside C, that was isolated from the aerial part of Astragalus lehmannianus Bunge (Leguminosae) was established as 20R,24S-epoxycycloartane-3β,6α, 16β,24-tetraol 3-O-[β-D-glucopyranosyl(1→2)]- β-D-glucopyranoside-25-O-β-D-glucopyranoside.

Biocatalysis of cycloastragenol by filamentous fungi to produce unexpected triterpenes

The biocatalysis of cycloastragenol, a natural tetracyclic triterpenoid with anti-aging activity, by cultured whole cells of three strains of filamentous fungi, namely Cunninghamella elegans AS 3.1207, Syncephalastrum racemosum AS 3.264 and Doratomyces stemonitis AS 3.1411 produced 15 metabolites. Thirteen of them are new compounds. The structures of these metabolites were fully characterized on the basis of HR-ESI-MS analyses together with 1D and 2D NMR spectroscopy. The three fungal strains exhibited significant biocatalytic preferences: C. elegans enabled hydroxylation reactions, particularly on the 28- and 29-CH3 groups; S. racemosum efficiently catalyzed a complicated rearrangement reaction to form the unusual ranunculane skeleton, which was further substituted with diverse side chains at C-19; D. stemonitis mainly led to carbonylation reactions, especially on 3-OH. It is particularly noteworthy that S. racemosum also catalyzed an unexpected ring expansion reaction to generate the rare 9(10)a-homo-19-nor-cycloartane skeleton. Biocatalysis was proved powerful in the structural diversification of cycloastragenol for future structure-activity relationship studies. Copyright

Compositions and Methods for Increasing Telomerase Activity

The present invention relates to methods and compositions for increasing telomerase activity in cells. Such compositions include pharmaceutical formulations. The methods and compositions are useful for treating diseases subject to treatment by an increase in telomerase activity in cells or tissue of a patient. They are also useful for enhancing replicative capacity of cells in culture, as in ex vivo cell therapy and for enhancing proliferation of stem and progenitor cells.

Triterpene glycosides from Astragalus and their genins. LXXVIII. Chemical transformation of cycloartanes. VI. Partial synthesis of cycloadsurgenina

Cycloadsurgenin, 20R,24 S-epoxycycloartan-6α,25-diol-3,16-dione, was partially synthesized in four steps from cyclosieversigenin. Side products with the structures 17E,24S-cycloart-17-en-6α,24,25-triol-3,16-dione and 17Z,24 S-cycloart-17-en-6α,24,25-triol

Triterpene glycosides from Tragacantha stipulosa and their genins. Structure of cyclostipuloside E

The known compound trojanoside A(1) and a new cycloartane glycoside cyclostipuloside E (2) were isolated from the aerial parts of Tragacantha stipulosa Boriss. The structure of cyclostipuloside E was proposed as 24R-cycloartan-3β,6α,16β,24,25-pentaol6,16,25-tri-O-β-D- glucopyranoside3-O-β-D-xylopyranoside based on physicochemical data and chemical transformations.

Triterpene glycosides of Astragalus and their genins. LXVII. Structure of cycloexoside B

Another seven components from the roots of Astragalus exilis A.Kor. (Leguminosae) were identified using spectral data and chemical transformations. A triterpenoid of genin nature was identical to cyclosiversigenin. One compound of glycosidic nature turned out to be a new cycloartane glycoside called by us cycloexoside B of structure 20R,24S-epoxycycloartan-3β,6α,16β ,25-tetraol 3-O-β-D-(2-O-acetyl)xylopyranoside. Five glycosides were identified as cyclosiversigenin 3-O-β-D-xylopyranoside and cyclosiversiosides B, C, D, and G.

Triterpene glycosides from Astragalus. Structure of cyclounifolioside B from Astragalus unifoliolatus

The previously known astrailienin A and the new cycloartane glycoside cyclounifolioside B with structure cyclosiversigenin 3-O-[β -D-glucopyranosyl(1→2)]-β-D-glucopyranoside were isolated from Astragalus unifoliolatus Bunge. The structures of these compounds were established using chemical transformations and two-dimensional spectra (ROESY, HMBC, HSQC, TOCSY, COSY).