Limonin

Limonin
Names
	Preferred IUPAC name (2aR,4aR,4bR,5aS,8S,8aS,10aR,10bR,14aS)-8-(Furan-3-yl)-2,2,4a,8a-tetramethyldecahydro-11H,13H-oxireno[2,3-c]pyrano[4′′,3′′:2′,3′]furo[3′,4′:5,6]naphtho[1,2-d]pyran-4,6,13(2H,5aH)-trione
	Other names Limonoate D-ring-lactone; Limonoic acid di-δ-lactone; 7,16-Dioxo-7,16-dideoxylimondiol;
Identifiers
CAS Number	1180-71-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16226 ;
ChEMBL	ChEMBL517449 ;
ChemSpider	156367 ;
ECHA InfoCard	100.236.039
PubChem CID	179651;
UNII	L0F260866S ;
CompTox Dashboard (EPA)	DTXSID8045985 ;
	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 Key: KBDSLGBFQAGHBE-MSGMIQHVSA-N ; 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). verify (what is ?) 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.

Sources

Limonin is enriched in citrus fruits and is often found at higher concentrations in seeds, for example orange and lemon seeds.^[1]

Presence in citrus products

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.^[2]

Research

Limonin is under basic research to assess its possible biological properties.^[1]

References

^ ^a ^b "Limonin". PubChem, US National Library of Medicine. 17 December 2022. Retrieved 21 December 2022.
^ Fayoux, S. P. C.; Hernandez, R. J.; Holland, R. V. (2007). "The Debittering of Navel Orange Juice Using Polymeric Films". Journal of Food Science. 72 (4): E143–E154. doi:10.1111/j.1750-3841.2007.00283.x. PMID 17995766.

External links

"Citrus Compound: ready to help your body!" (Agricultural Research Service, USDA)

[pubchem-1] "Limonin". PubChem, US National Library of Medicine. 17 December 2022. Retrieved 21 December 2022.

[2] Fayoux, S. P. C.; Hernandez, R. J.; Holland, R. V. (2007). "The Debittering of Navel Orange Juice Using Polymeric Films". Journal of Food Science. 72 (4): E143–E154. doi:10.1111/j.1750-3841.2007.00283.x. PMID 17995766.

[1]

[2]

Names


Preferred IUPAC name (2aR,4aR,4bR,5aS,8S,8aS,10aR,10bR,14aS)-8-(Furan-3-yl)-2,2,4a,8a-tetramethyldecahydro-11H,13H-oxireno[2,3-c]pyrano[4′′,3′′:2′,3′]furo[3′,4′:5,6]naphtho[1,2-d]pyran-4,6,13(2H,5aH)-trione
Other names Limonoate D-ring-lactone Limonoic acid di-δ-lactone 7,16-Dioxo-7,16-dideoxylimondiol
Identifiers
CAS Number	1180-71-8^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16226^Y
ChEMBL	ChEMBL517449^N
ChemSpider	156367^Y
ECHA InfoCard	100.236.039
PubChem CID	179651
UNII	L0F260866S^Y
CompTox Dashboard (EPA)	DTXSID8045985
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 verify (what is ^YN ?) Infobox references