| Identification | More | [Name]
Dehydrocostus lactone | [CAS]
477-43-0 | [Synonyms]
DEHYDROCOSTUSLACTONE
EPILIGULYL OXIDE
DEHYDROCOSTUS LACTONE hplc
(3aS,6aR,9aR,9bS)-Decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one
DEHYDROCOSTUNOLIDE
Azuleno[4,5-b]furan-2(3H)-one,decahydro-3,6,9-
Costus lactone, dehydro-
tris(methylene)-,(3aS,6aR,9aR,9bS)-
(3aS)-3,6,9-Tris(methylene)-2,3,3a,4,5,6,6aβ,7,8,9,9aβ,9bα-dodecahydroazuleno[4,5-b]furan-2-one
(3aS,6aβ,9aβ,9bα)-Dodecahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2-one
3aβ,4,5,6,6aβ,7,8,9,9aβ,9bα-Decahydro-3,6,9-trismethyleneazuleno[4,5-b]furan-2(3H)-one | [EINECS(EC#)]
225-472-7 | [Molecular Formula]
C15H18O2 | [MDL Number]
MFCD00210277 | [Molecular Weight]
230.3 | [MOL File]
477-43-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
57.0 to 61.0 °C | [Boiling point ]
140-143 °C(Press: 0.5 Torr) | [density ]
1.09 | [storage temp. ]
room temp | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [color ]
White to Off-White | [Odor]
nutty | [Optical Rotation]
[α]/D -14.0±3.0°, c = 1 in chloroform | [λmax]
206nm(MeOH)(lit.) | [InChI]
InChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2/t11-,12-,13-,14-/m0/s1 | [Contact allergens]
A guaianolide sesquiterpene lactone extracted from costus oil. It is one of the components of Lactone mix, with costunolide and alantolactone, used to detect Compositae-sensitive patients. | [InChIKey]
NETSQGRTUNRXEO-XUXIUFHCSA-N | [SMILES]
O1C(=O)C(=C)[C@]2([H])CCC(=C)[C@@]3([H])[C@@]([H])([C@@]12[H])C(=C)CC3 | [LogP]
1.480 (est) | [CAS DataBase Reference]
477-43-0(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Definition]
ChEBI: An organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in which the hydroxy group and the carboxy group have undergone
formal condensation to afford the corresponding gamma-lactone. | [Description]
A guaianolide sesquiterpene lactone extracted from
costus oil. Dehydrocostuslactone is one of the components
of lactone-mix, with costunolide and alantolactone,
used to detect Compositae-sensitive patients.
| [Chemical Properties]
It is soluble in solvents such as ethyl acetate, acetone, and DMSO, but insoluble in water. It is derived from the plant Vladimiria souliei (Franch.) Ling of the Asteraceae family. | [Uses]
Dehydrocostus lactone is the oil extracted from Saussurea lappa is used in perfumery and in the Orient for all kinds of diseases. | [References]
[1] MADAN MOHAN PANDEY Ajay K S R Subha Rastogi. Saussurea costus: Botanical, chemical and pharmacological review of an ayurvedic medicinal plant[J]. Journal of ethnopharmacology, 2007, 110 3: Pages 379-390. DOI: 10.1016/j.jep.2006.12.033
[2] CHIH-YA WANG. Dehydrocostuslactone suppresses angiogenesis in vitro and in vivo through inhibition of Akt/GSK-3β and mTOR signaling pathways.[J]. PLoS ONE, 2012: e31195. DOI: 10.1371/journal.pone.0031195
[3] BIRGIT LOHBERGER. Sesquiterpene lactones downregulate G2/M cell cycle regulator proteins and affect the invasive potential of human soft tissue sarcoma cells.[J]. PLoS ONE, 2013: e66300. DOI: 10.1371/journal.pone.0066300
[4] XUEJING LIN Changqing S Zhangxiao Peng. Potential anti-cancer activities and mechanisms of costunolide and dehydrocostuslactone.[J]. International Journal of Molecular Sciences, 2015, 16 5: 10888-10906. DOI: 10.3390/ijms160510888
[5] ELENA BUTTURINI. Two naturally occurring terpenes, dehydrocostuslactone and costunolide, decrease intracellular GSH content and inhibit STAT3 activation.[J]. PLoS ONE, 2011: e20174. DOI: 10.1371/journal.pone.0020174
[6] CLAUDIA SCARPONI. Inhibition of inflammatory and proliferative responses of human keratinocytes exposed to the sesquiterpene lactones dehydrocostuslactone and costunolide.[J]. ACS Applied Bio Materials, 2014: e107904. DOI: 10.1371/journal.pone.0107904 |
|
|