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 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

Chemical compound

Not to be confused with Limonene.

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

[edit]

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

[edit]

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

[edit]

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

## References

[edit]

1. ^ a b "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.

## External links

[edit]

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

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency