3,8-Dihydrodiligustilide

3,8-Dihydrodiligustilide
Clinical data
Other names	(3Z')-(3a'R,6'R,3R,6R,7R)-3,8-Dihydro-6.6',7.3a'-diligustilide
Identifiers
	IUPAC name (1S,2S,6Z,10S,11S)-16-Butyl-6-butylidene-5,15-dioxapentacyclo[9.5.2.01,13.02,10.03,7]octadeca-3(7),12-diene-4,14-dione;
PubChem CID	102175205;
Chemical and physical data
Formula	C24H30O4
Molar mass	382.500 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCC1[C@]23CC[C@H](C=C2C(=O)O1)[C@H]4[C@@H]3C5=C(CC4)/C(=C/CCC)/OC5=O;
	InChI InChI=1S/C24H30O4/c1-3-5-7-18-16-10-9-15-14-11-12-24(21(15)20(16)23(26)27-18)17(13-14)22(25)28-19(24)8-6-4-2/h7,13-15,19,21H,3-6,8-12H2,1-2H3/b18-7-/t14-,15+,19?,21-,24+/m1/s1; Key:YTEUTQUNVHWZOR-LGNHLWLRSA-N;

3,8-Dihydrodiligustilide is a nonsteroidal phytoprogestogen that is found in Ligusticum chuanxiong.^[1]^[2] It is a potent agonist of the progesterone receptor (EC₅₀ = 90 nM).^[1] Another compound in the plant, riligustilide, is also a phytoprogestogen, but is almost 1,000-fold less potent and is very weak in comparison (EC₅₀ ≈ 81 μM).^[1]

References

^ ^a ^b ^c ^d Lim LS, Shen P, Gong YH, Yong EL (2006). "Dimeric progestins from rhizomes of Ligusticum chuanxiong". Phytochemistry. 67 (7): 728–34. Bibcode:2006PChem..67..728L. doi:10.1016/j.phytochem.2006.01.024. PMID 16516938.
^ Ahmed HM, Yeh JY, Lin WJ, Forsberg NE, Cheng WT, Ou BR (2014). "Validation of a luciferase bioassay to detect the progestative activity in gilts whose estrus was induced by an uterotonic herb (Ligusticum chuanxiong)". Livestock Science. 163: 159–164. doi:10.1016/j.livsci.2014.02.012. ISSN 1871-1413.

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