Dehydrocostus lactone Chemical Properties

Melting point:

57.0 to 61.0 °C

Boiling point:

140-143 °C(Press: 0.5 Torr)

Density 

1.09

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

color 

White to Off-White

Odor

nutty

optical activity

[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

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)

Safety Information

Safety Statements 

24/25

HS Code 

29322090

Dehydrocostus lactone Usage And Synthesis

Description

Dehydrocostus lactone is a natural sesquiterpene first isolated from costus root, which is used in traditional medicine. Dehydrocostus lactone has diverse anti-cancer properties in cells and animal models, causing cell cycle arrest, inducing apoptosis, diminishing multidrug resistance, and suppressing angiogenesis in cancer cells. It also has anti-inflammatory actions in cells, including the inhibition of signaling through STAT1 and STAT3.

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

Soluble in ethyl acetate, acetone, DMSO and other solvents, insoluble in water. Derived from Chuanmuxiang [Vladimiria souliei(Franch.)Ling], family Asteraceae.

Uses

Dehydrocostus lactone is the oil extracted from Saussurea lappa is used in perfumery and in the Orient for all kinds of diseases.

Uses

Dehydrocostus Lactone is a compound known to be a growth regulator in plants. Known to affect cell viability and cell cycle distribution it may be useful in the application towards drug-resistant tumors.

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.

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.

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

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