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SML1929

Equisetin

Name: Equisetin
Brand: SIGMA

(Fusarium equiseti), ≥97% (HPLC)

Synonym(s):

(3E,5S)-3-[[(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(E)-prop-1-enyl]-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-hydroxymethylidene]-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₃₁NO₄

CAS Number:

57749-43-6

Molecular Weight:

373.49

NACRES:

NA.77

UNSPSC Code:

12352200

Assay:

≥97% (HPLC)

Form:

powder

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Properties

Quality Segment

200

biological source

(Fusarium equiseti)

assay

≥97% (HPLC)

form

powder

solubility

DMSO: soluble 1 mg/mL, chloroform: soluble 5 mg/mL

shipped in

ambient

storage temp.

−20°C

SMILES string

C[C@H]1C[C@]2([H])[C@@]([C@](C)(/C(O)=C3C([C@H](CO)N(C)C/3=O)=O)[C@H](/C=C/C)C=C2)([H])CC1

InChI

1S/C22H31NO4/c1-5-6-15-9-8-14-11-13(2)7-10-16(14)22(15,3)20(26)18-19(25)17(12-24)23(4)21(18)27/h5-6,8-9,13-17,24,27H,7,10-12H2,1-4H3/b6-5+/t13-,14-,15-,16-,17+,22-/m1/s1

InChI key

SLOQQJFOWFUUMP-KNQICWOTSA-N

Description

Biochem/physiol Actions

Equisetin is a tetramic acid analog derived from Fusarium equisti. Equisetin is mainly known for its antibiotic and cytotoxic activity and for its inhibitory effect on HIV-1 integrase. Inhibition of HIV integrase by Equisetin was reported with IC₅₀ values of 5-20 μM. Moreover, it was shown that Equisetin specifically inhibits the substrate anion carriers of the inner membrane of mitochondria and acts nonspecifically on protein membranes and protein hydrophobic domains. In addition, it was demonstrated that Equisetin causes phytotoxicity by causing root Necrosis and was also identified in a mycotoxin cocktail associated with cattle feeding problems.

Equisetin is a tetramic acid analog derived from Fusarium equisti.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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