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Evodine - 97.5%(HPLC), high purity , CAS No.1180-71-8
Basic Description
Synonyms
CAS-1180-71-8 | Limonoic acid, di-.delta.-lactone | Linonin | NCGC00263659-01 | AKOS015965307 | NCGC00178483-05 | NSC36508 | NSC-36508 | Tox21_111513_1 | 3-furyl(tetramethyl)[?]trione | Limonin | (1R,2R,7S,10R,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,2
Specifications & Purity
≥97.5%(HPLC)
Biochemical and Physiological Mechanisms
Limonin is a triterpenoid aglycone that is a bitter principle of citrus fruits. Limonin is chemically induced carcinogenesis inhibitor and HIV-1 replication inhibitor. Limonin has anti-proliferative, proapoptotic activity on several cance
Storage Temp
Store at 2-8°C
Shipped In
Wet ice
This product requires cold chain shipping. Ground and other economy services are not available.
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Lipids and lipid-like molecules
Class
Prenol lipids
Subclass
Triterpenoids
Intermediate Tree Nodes
Not available
Direct Parent
Limonoids
Alternative Parents
Steroid lactones 11-oxosteroids Naphthopyrans Naphthalenes 1,4-dioxepanes Delta valerolactones Pyrans Oxanes Dicarboxylic acids and derivatives Tetrahydrofurans Heteroaromatic compounds Furans Carboxylic acid esters Ketones Dialkyl ethers Epoxides Oxacyclic compounds Hydrocarbon derivatives Organic oxides
Molecular Framework
Aromatic heteropolycyclic compounds
Substituents
Limonoid skeleton - Steroid lactone - 11-oxosteroid - Oxosteroid - 2-oxosteroid - Steroid - Naphthopyran - Naphthalene - Delta valerolactone - Dioxepane - 1,4-dioxepane - Delta_valerolactone - Pyran - Oxane - Dicarboxylic acid or derivatives - Tetrahydrofuran - Heteroaromatic compound - Furan - Carboxylic acid ester - Lactone - Ketone - Organoheterocyclic compound - Carboxylic acid derivative - Oxacycle - Dialkyl ether - Oxirane - Ether - Organooxygen compound - Organic oxide - Carbonyl group - Hydrocarbon derivative - Organic oxygen compound - Aromatic heteropolycyclic compound
Description
This compound belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
External Descriptors
Limonoids
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
Pubchem Sid
504757704
Pubchem Sid Url
https://pubchem.ncbi.nlm.nih.gov/substance/504757704
IUPAC Name
(1R,2R,7S,10R,13R,14R,16S,19S,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
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
Smiles
CC1(C2CC(=O)C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)C
Isomeric SMILES
C[C@@]12CC[C@H]3[C@]([C@@]14[C@H](O4)C(=O)O[C@H]2C5=COC=C5)(C(=O)C[C@@H]6[C@@]37COC(=O)C[C@@H]7OC6(C)C)C
WGK Germany
3
Molecular Weight
470.51
Reaxy-Rn
1632660
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1632660&ln=
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Solubility
Insoluble in water; Soluble in Tetrahydrofuran,Acetone; Very slightly soluble in Alcohol,Ether
Sensitivity
Heat Sensitive
Specific Rotation[α]
-117° (C=1,Acetone)
Melt Point(°C)
271-272°C
Molecular Weight
470.500 g/mol
XLogP3
1.800
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
1
Exact Mass
470.194 Da
Monoisotopic Mass
470.194 Da
Topological Polar Surface Area
105.000 Ų
Heavy Atom Count
34
Formal Charge
0
Complexity
1010.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
9
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Citations of This Product
1.
Dan Yu, Fei Liu, Changdong Zou, Xiao Yang.
(2023)
Municipal green waste promotes iron release from steelmaking slag in water. RESOURCES CONSERVATION AND RECYCLING,
188
(106722).
2.
Qi Quan, Wei Liu, Jiajing Guo, Meiling Ye, Juhua Zhang.
(2022)
Effect of Six Lactic Acid Bacteria Strains on Physicochemical Characteristics, Antioxidant Activities and Sensory Properties of Fermented Orange Juices. Foods,
11
(13):
(1920).
3.
Xiao Tu, Chenxi Duan, Siwei Wu, Shengli Fu, Jianmin Ye.
(2021)
Identification of plumbagin as an effective chemotherapeutic agent for treatment of Gyrodactylus infections. AQUACULTURE,
535
(736372).
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3 Citations
D2129052