6754-13-8 Usage
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 6754-13-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,7,5 and 4 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 6754-13:
(6*6)+(5*7)+(4*5)+(3*4)+(2*1)+(1*3)=108
108 % 10 = 8
So 6754-13-8 is a valid CAS Registry Number.
InChI:InChI=1/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
6754-13-8Relevant articles and documents
Helenanolides: Stereocontrolled Total Synthesis of dl-Bigelovin, dl-Mexicanin I, and dl-Linifolin A
Grieco, Paul A.,Ohfune, Yasufumi,Majetich, George F.
, p. 360 - 366 (2007/10/02)
Stereocontrolled total syntheses of the sesquiterpene lactones dl-bigelovin (11), dl-mexicanin I (12), and dl-linifolin A (13) are described.The syntheses start with the hydroazulenone 4 and proceed via the key epoxy alkohol 9.Elaboration of 9 into the tricyclic γ-lactone 14 dl-bigelovin. α-methylenation.Subsequent oxidation at C(4) completes the synthesis of dl-bigelovin.Epoxide opening of 9 with dilithioacetate provides access to tricyclic lactone 23 which gives way to 24 via reduction of ketone 25.Cleavage of the benzyl ether in 24 followed by α-methylenationand oxidation generates dl-mexicanin I.Acetylation of 12 affords dl-linifolin A.
