HELENALIN

HELENALIN Basic information
Product Name:HELENALIN
Synonyms:(3as-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-ethyl-3-methylene;HELENALIN(SH);HELENALIN;6alpha,8beta-dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oicacid12,8-lactone;a-dimethyl-3-methyleneazuleno[6,5-b]-furan-2,5-dione;ambrosa-2,11(13)-dien-12-oicacid,6-alpha,8-beta-dihydroxy-4-oxo-,12,8-lacton;ambrosa-2,11(13)-dien-12-oicacid,6alpha,8beta-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-dim
CAS:6754-13-8
MF:C15H18O4
MW:262.3
EINECS:
Product Categories:Miscellaneous Natural Products
Mol File:6754-13-8.mol
HELENALIN Structure
HELENALIN Chemical Properties
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).
pka13.29±0.60(Predicted)
form White to off-white solid.
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.
LogP0.870
Safety Information
RIDADR 2811
HazardClass 6.1(b)
PackingGroup III
Hazardous Substances Data6754-13-8(Hazardous Substances Data)
ToxicityLD50 in mice, rats (mg/kg): 150, 125 orally (Witzel)
MSDS Information
HELENALIN Usage And Synthesis
DescriptionHelenalin (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
UsesHelenalin 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.
DefinitionChEBI: 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+4°C
References1) 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
HELENALIN Preparation Products And Raw materials
BAY 11-7085 5-Aminosalicylic acid Rocaglamide I panepoxydone 3'-Hydroxyrocaglamide 6-AMINO-4-(4-PHENOXYPHENYLETHYLAMINO)QUINAZOLINE helenalin methacrylate 1-HYDROXYMETHYL-3-CYCLOPENTENE HELENALIN Helenalin, A. chamissonis ssp. foliosa HELENALIN(RG) Florilenalin ETHYL 6-KETO-7-OCTENOATE 5-ETHYL-3-METHYLENE-DIHYDRO-FURAN-2-ONE bis(helenalinyl)malonate N-NONYL ACRYLATE Autumnolide HELENALIN(REAGENT / STANDARD GRADE)

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