Limonin

Limonin

Names
IUPAC name 7,16-Dioxo-7,16-dideoxylimondiol
Other names limonoate D-ring-lactone, limonoic acid di-delta-lactone
Identifiers
CAS Number	1180-71-8 N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16226 Y
ChemSpider	156367 Y
ECHA InfoCard	100.236.039
PubChem CID	179651
InChI InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1 Y Key: KBDSLGBFQAGHBE-MSGMIQHVSA-N Y InChI=1/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1 Key: KBDSLGBFQAGHBE-MSGMIQHVBF
SMILES O=C4[C@@]6(C)[C@@]72O[C@@H]7C(=O)O[C@@H](c1ccoc1)[C@]2(C)CC[C@@H]6[C@]35COC(=O)C[C@@H]5OC([C@@H]3C4)(C)C
Properties
Chemical formula	C26H30O8
Molar mass	470.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Limonin is a limonoid, and a bitter, white, crystalline substance found in citrus and other plants. It is also known as limonoate D-ring-lactone and limonoic acid di-delta-lactone. Chemically, it is a member of the class of compounds known as furanolactones.

Limonin is enriched in citrus fruits and is often found at higher concentrations in seeds, for example orange and lemon seeds. Limonin is also present in plants such as those of the Dictamnus genus.

Limonin and other limonoid compounds contribute to the bitter taste of some citrus food products. Researchers have proposed removal of limonoids from orange juice and other products (known as "debittering") through the use of polymeric films.

Ongoing research programs are examining the effects of limonin in human diseases. Citrus seed extracts reportedly have antiviral properties, inhibiting replication of retroviruses like HIV-1 and HTLV-I. Neuroprotective effects of limonin have also been described. Limonin reduces proliferation of colon cancer cells and has been tested as an anti-obesity agent in mice.