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1180-71-8 molecular structure
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(1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0^{2,7}.0^{2,10}.0^{14,16}.0^{14,20}]docosane-5,12,17-trione

ChemBase ID: 72956
Molecular Formular: C26H30O8
Molecular Mass: 470.5116
Monoisotopic Mass: 470.19406792
SMILES and InChIs

SMILES:
C1(=O)O[C@H]([C@]2([C@]3([C@@H]1O3)[C@]1([C@H](CC2)[C@]23[C@@H](CC1=O)C(O[C@H]2CC(=O)OC3)(C)C)C)C)c1cocc1
Canonical SMILES:
O=C1OC[C@]23[C@H](C1)OC([C@@H]2CC(=O)[C@@]1([C@@H]3CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@H]2c1cocc1)C)C)(C)C
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
InChIKey:
KBDSLGBFQAGHBE-MSGMIQHVSA-N

Cite this record

CBID:72956 http://www.chembase.cn/molecule-72956.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0^{2,7}.0^{2,10}.0^{14,16}.0^{14,20}]docosane-5,12,17-trione
(1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-trione
(1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0?,?.0?,??.0??,??.0??,??]docosane-5,12,17-trione
IUPAC Traditional name
limonin
Synonyms
Limonin
Limonin
limonoate D-ring-lactone
limonoic acid di-delta-lactone
Limonoic acid 3,19:16,17 dilactone
CAS Number
1180-71-8
MDL Number
MFCD00075922
PubChem SID
24896458
162037876
PubChem CID
179651
CHEBI ID
16226
Chemspider ID
156367
Wikipedia Title
Limonin

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 17.60684  H Acceptors
H Donor LogD (pH = 5.5) 2.4571912 
LogD (pH = 7.4) 2.4571912  Log P 2.4571912 
Molar Refractivity 114.7192 cm3 Polarizability 46.453953 Å3
Polar Surface Area 104.57 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Apperance
Powder expand Show data source
Melting Point
298-300°C expand Show data source
Storage Condition
-20°C expand Show data source
2-8°C expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
>90% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Biological Source
from citrus seeds expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02193765 external link
From Citrus Seeds
A natural compound found in grapefruit and other citrus seeds. It has been shown to inhibit chemically induced carcinogenesis and demonstrates anti-feedant properties.
Selleck Chemicals - S2319 external link
Research Area: Inflammation
Biological Activity:
Limonin 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. [1]
Sigma Aldrich - L9647 external link
Biochem/physiol Actions
Limonin is a triterpenoid aglycone that is a bitter principle of citrus fruits. It has anti-proliferative, proapoptotic activity on several cancer cell lines and inhibits azoxymethane-induced colon cancer in rats. It also inhibits HIV-1 replication in culturedf monocytes, macrophages, and mononuclear cells, perhaps by inhibition of HIV-1 protease activity.
General description
Limonin may be used in assays to quantify limonin in citrus products. It may also be used in other assays as a control, standard, or competitor or in studies on the physiology, metabolism, and biosynthesis of limonin.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Altieri, M.A., et al., Protect. Ecol. , 6 : 91, (1984).
  • • http://en.wikipedia.org/wiki/Limonin
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PATENTS

PATENTS

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INTERNET

INTERNET

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