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SML1448

Sigma-Aldrich

Cycloastragenol

≥98% (HPLC)

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Synonym(s):
Astramembrangenin, Cyclosieversigenin, Cyclosiversigenin, GRN510, TAT2, (3β,6α,16β,20R,24S)-20,24-Epoxy-9,19-cyclolanostane-3,6,16,25-tetrol, Cyclogalegigenin
Empirical Formula (Hill Notation):
C30H50O5
CAS Number:
78574-94-4
Molecular Weight:
490.72
MDL number:
MFCD24849201
UNSPSC Code:
12352200
PubChem Substance ID:
329825888
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +45 to +60°, c = 1 in methanol

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

C[C@]1(O[C@H](C(O)(C)C)CC1)[C@@]2([H])[C@@H](O)C[C@@]3(C)[C@]4([H])C[C@H](O)[C@@]5([H])C(C)(C)[C@@H](O)CC[C@]5(C6)[C@]46CC[C@@]32C

InChI

1S/C30H50O5/c1-24(2)20(33)8-11-30-16-29(30)13-12-26(5)23(28(7)10-9-21(35-28)25(3,4)34)18(32)15-27(26,6)19(29)14-17(31)22(24)30/h17-23,31-34H,8-16H2,1-7H3/t17-,18-,19-,20-,21-,22-,23-,26+,27-,28+,29-,30+/m0/s1

InChI key

WENNXORDXYGDTP-UOUCMYEWSA-N

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General description

Cycloastragenol is isolated from Astragalus species.

Biochem/physiol Actions

Cycloastragenol is an aglycone of astragaloside IV isolated from Astragalus species that exhibits anti-inflammatory properties and promotes and wound gap closure. Cycloastragenol enhances the antiviral response in human CD8+ T-lymphocytes. Cycloastragenol induces telomerase activity and induces CREB (cAMP response element binding) activation in human neonatal keratinocytes, PC12 cells, and primary neurons.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Claude Jourdan Le Saux et al.
PloS one, 8(3), e58423-e58423 (2013-03-22)
The emergence of diseases associated with telomere dysfunction, including AIDS, aplastic anemia and pulmonary fibrosis, has bolstered interest in telomerase activators. We report identification of a new small molecule activator, GRN510, with activity ex vivo and in vivo. Using a
Steven Russell Fauce et al.
Journal of immunology (Baltimore, Md. : 1950), 181(10), 7400-7406 (2008-11-05)
Telomerase reverse transcribes telomere DNA onto the ends of linear chromosomes and retards cellular aging. In contrast to most normal somatic cells, which show little or no telomerase activity, immune cells up-regulate telomerase in concert with activation. Nevertheless, during aging
Fanny C F Ip et al.
Neuro-Signals, 22(1), 52-63 (2014-08-07)
Cycloastragenol (CAG) is an aglycone of astragaloside IV. It was first identified when screening Astragalus membranaceus extracts for active ingredients with antiaging properties. The present study demonstrates that CAG stimulates telomerase activity and cell proliferation in human neonatal keratinocytes. In

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