3,8-dihydrodiligustilide

3,8-Dihydrodiligustilide

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
Synonyms	(3Z')-(3a'R,6'R,3R,6R,7R)-3,8-Dihydro-6.6',7.3a'-diligustilide
PubChem CID	102175205
Chemical and physical data
Formula	C24H30O4
Molar mass	382.5 g/mol
3D model (Jmol)	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. It is a potent agonist of the progesterone receptor (EC₅₀ = 90 nM). 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).