| Identification | Back Directory | [Name]
HELENALIN | [CAS]
6754-13-8 | [Synonyms]
Helelin
NSC 85236
HELENALIN
HELENALIN(SH)
HELENALIN USP/EP/BP
Helenalin
(NSC 85236)
a-dimethyl-3-methyleneazuleno[6,5-b]-furan-2,5-dione
(3as-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-ethyl-3-methylene
6alpha,8beta-dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oicacid12,8-lactone
ambrosa-2,11(13)-dien-12-oicacid,6alpha,8beta-dihydroxy-4-oxo-,12,8-lactone
ambrosa-2,11(13)-dien-12-oicacid,6-alpha,8-beta-dihydroxy-4-oxo-,12,8-lacton
azuleno(6,5-b)furan-2,5-dione,3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dim
[3as]-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-octahydro-4-hydroxy-4abeta,8alph
(3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
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)- | [Molecular Formula]
C15H18O4 | [MDL Number]
MFCD01674580 | [MOL File]
6754-13-8.mol | [Molecular Weight]
262.3 |
| Chemical Properties | Back Directory | [Melting point ]
167-168° | [alpha ]
D25 -102.8° (c = 3.64 in 95% ethanol) | [Boiling point ]
325.55°C (rough estimate) | [density ]
1.0772 (rough estimate) | [refractive index ]
1.4300 (estimate) | [storage temp. ]
-20° | [solubility ]
Soluble in DMSO (up to 20 mg/ml) or in Ethanol (up to 10 mg/ml). | [form ]
White to off-white solid. | [pka]
13.29±0.60(Predicted) | [color ]
White | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month. | [LogP]
0.870 |
| Hazard Information | Back Directory | [Description]
Helenalin (6754-13-8) is a novel sesquiterpene lactone which inhibits NFκB1?and displays potent anti-inflammatory activity2. It suppresses essential immune functions of activated CD4+ T cells by multiple mechanisms.3 Helenalin also inhibits telomerase and this activity may be partially responsible for its anti-tumor effects.4 | [Uses]
Helenalin is a highly toxic compound, with hepatic and lymphatic tissues particularly vulnerable to its effects. It is believed to be responsible for the toxicity and skin irritation associated with Arnica. If enough of the plant is ingested, the helenalin produces severe gastroenteritis and internal bleeding of the digestive tract. | [Definition]
ChEBI: Helenalin is a sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer). It has a role as an anti-inflammatory agent, an antineoplastic agent, a plant metabolite and a metabolite. It is a gamma-lactone, a cyclic ketone, an organic heterotricyclic compound, a sesquiterpene lactone and a secondary alcohol. | [storage]
Store at -20°C | [References]
1) Lyss?et al. (1998),?The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65; J. Biol. Chem.,?273?33508
2) Lyss?et al. (1997),?Helenalin, an anti-inflammatory sesquiterpene lactone from Arnica, selectively inhibits transcription factor NF-κB; Biol. Chem.,?278?951
3) Berges?et al. (2009),?Helenalin suppresses essential immune functions of activated CD4+ T cells by multiple mechanisms; Mol. Immunol.,?46?2892
4) Huang?et al. (2005),?Potent inhibition of human telomerase by helenalin; Cancer Lett.,?227?169 |
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