CAS 6754-13-8

Helenalin

Description:

Helenalin is a naturally occurring sesquiterpene lactone primarily derived from the plant species *Arnica montana* and other members of the Asteraceae family. It is characterized by its yellow crystalline appearance and has a molecular formula of C15H18O3. Helenalin exhibits a range of biological activities, including anti-inflammatory, analgesic, and antimicrobial properties, making it of interest in pharmacological research. Its mechanism of action is thought to involve the inhibition of pro-inflammatory cytokines and the modulation of various signaling pathways. Additionally, helenalin has been studied for its potential anticancer effects, as it can induce apoptosis in certain cancer cell lines. However, it is important to note that helenalin can also exhibit cytotoxicity at higher concentrations, which necessitates careful consideration in therapeutic applications. Due to its bioactive nature, helenalin is often explored in the context of herbal medicine and natural product chemistry.

Formula: C₁₅H₁₈O₄

InChI: InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1

InChI key: InChIKey=ZVLOPMNVFLSSAA-XEPQRQSNSA-N

SMILES: C[C@@]12[C@]([C@H](C)C[C@@]3([C@]([C@@H]1O)(C(=C)C(=O)O3)[H])[H])(C=CC2=O)[H]

Synonyms:

• (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-Octahydro-4-hydroxy-4abeta,8 alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione
• (3aS,4S,4aR,7aR,8R,9aR)-3,3a,4,4a,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-3-methyleneazuleno[6,5-b]furan-2,5-dione
• (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
• 6alpha,8beta-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone
• Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone
• Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone
• Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone (8CI)
• Ambrosa-2,11(13)-dien-12-oic acid, 6α,8β-dihydroxy-4-oxo-, 12,8-lactone
• Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-
• Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))- (9CI)
• Azuleno[6,5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS,4S,4aR,7aR,8R,9aR)-
• Azuleno[6,5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3aα,4α,4aβ,7aα,8α,9aα)]-
• Brn 0028081
• Helenalin A
• Hsdb 3490
• Nsc 85236
• Pf 56
• Helenalin

Helenalin

CAS: 6754-13-8

Helenalin: anti-inflammatory sesquiterpene, inhibits NF-κB by alkylating p65 cysteine groups, blocks DNA binding.

Formula: C₁₅H₁₈O₄

Purity: 98%

Color and Shape: Solid

Molecular weight: 262.3

Ref: TM-T15467

Helenalin

CAS: 6754-13-8

Formula: C₁₅H₁₈O₄

Purity: ≥ 97.0%

Color and Shape: White to off-white solid

Molecular weight: 262.3

Ref: 7W-GL2626

Helenalin

CAS: 6754-13-8

Helenalin is a sesquiterpene lactone, which is a secondary metabolite derived from plants, specifically from the Arnica species. This compound is characterized by its molecular framework containing a cyclodecadiene ring along with an α-methylene-γ-lactone ring, conferring its biological activities. Helenalin exerts its effects primarily by inhibiting key transcription factors such as NF-κB and other molecules involved in critical signaling pathways. This mode of action results from its ability to form adducts with thiol groups of cysteine residues on these proteins, thus altering their activity and inhibiting inflammatory responses.

Purity: Min. 95%

Ref: 3D-FH177939

Helenalin

CAS: 6754-13-8

Formula: C₁₅H₁₈O₄

Molecular weight: 262.31

Ref: 4Z-H-111