Limonin glucoside - ≥95% , CAS No.123564-61-4

CAS: 123564-61-4 Cat. No.: L275342 Molecular Weight: 650.67 PubChem CID: 24820753

GRADE & PURITY ≥95%

Synonyms

LIMONOIC ACID, 17-O-.BETA.-D-GLUCOPYRANOSYL-, .DELTA.-LACTONE | AKOS040748750 | C06740 | limonin 17-beta-D-glucoside | 9553Q8Z7PF | Glucosyl-limonin | Limonin 17-beta-D-glucopyranoside | UNII-9553Q8Z7PF | LIMONIN 17-.BETA.-D-GLUCOPYRANOSIDE | SPIRO(9H,11H

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Store at +4°C. The product can be stored for up to 12 months.

Specifications

Synonyms

LIMONOIC ACID, 17-O-.BETA.-D-GLUCOPYRANOSYL-, .DELTA.-LACTONE | AKOS040748750 | C06740 | limonin 17-beta-D-glucoside | 9553Q8Z7PF | Glucosyl-limonin | Limonin 17-beta-D-glucopyranoside | UNII-9553Q8Z7PF | LIMONIN 17-.BETA.-D-GLUCOPYRANOSIDE | SPIRO(9H, 11H

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

Apoptotic agent. Limonin derivative. Aromatase inhibitor. Induces mitochondria mediated intrinsic apoptosis. Shows antiproliferative activity. Orally active.

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CC1(C2CC(=O)C3(C(C24COC(=O)CC4O1)CCC(C35C(O5)C(=O)O)(C)C(C6=COC=C6)OC7C(C(C(C(O7)CO)O)O)O)C)C
• IUPAC Name: (1R,2R,2'S,5S,6R,7R,10R,13S)-5-[(S)-furan-3-yl-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5,7,11,11-tetramethyl-8,15-dioxospiro[12,16-dioxatetracyclo[8.7.0.01,13.02,7]heptadecane-6,3'-oxirane]-2'-carboxylic acid
• InChIKey: FYIKIBQJAJRKQM-WNCNYDOCSA-N
• INCHI: 1S/C32H42O14/c1-28(2)17-9-18(34)30(4)16(31(17)13-42-20(35)10-19(31)45-28)5-7-29(3,32(30)25(46-32)26(39)40)24(14-6-8-41-12-14)44-27-23(38)22(37)21(36)15(11-33)43-27/h6,8,12,15-17,19,21-25,27,33,36-38H,5,7,9-11,13H2,1-4H3,(H,39,40)/t15-,16+,17+,19+,21-,22+,23-,24+,25-,27+,29+,30+,31-,32-/m1/s1
• Isomeric SMILES: C[C@]1(CC[C@H]2[C@]([C@@]13[C@H](O3)C(=O)O)(C(=O)C[C@@H]4[C@@]25COC(=O)C[C@@H]5OC4(C)C)C)[C@H](C6=COC=C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• PubChem CID: 24820753
• Molecular Weight: 650.67

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Triterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Triterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Limonoids
• Alternative Parents: Hexoses O-glycosyl compounds Delta valerolactones Dicarboxylic acids and derivatives Oxanes Oxirane carboxylic acids Heteroaromatic compounds Furans Tetrahydrofurans Ketones Secondary alcohols Carboxylic acid esters Oxacyclic compounds Acetals Dialkyl ethers Carboxylic acids Polyols Organic oxides Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Limonoid skeleton - Hexose monosaccharide - O-glycosyl compound - Glycosyl compound - Delta valerolactone - Delta_valerolactone - Dicarboxylic acid or derivatives - Oxirane carboxylic acid or derivatives - Oxirane carboxylic acid - Oxane - Monosaccharide - Tetrahydrofuran - Heteroaromatic compound - Furan - Secondary alcohol - Ketone - Carboxylic acid ester - Lactone - Acetal - Carboxylic acid derivative - Carboxylic acid - Dialkyl ether - Oxirane - Ether - Oxacycle - Organoheterocyclic compound - Polyol - Hydrocarbon derivative - Alcohol - Organic oxygen compound - Organic oxide - Primary alcohol - Carbonyl group - Organooxygen 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.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in water
• Molecular Weight: 650.700 g/mol
• XLogP3: -0.600
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 6
• Exact Mass: 650.257 Da
• Monoisotopic Mass: 650.257 Da
• Topological Polar Surface Area: 215.000 Ų
• Heavy Atom Count: 46
• Formal Charge: 0
• Complexity: 1290.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 14
• 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