Ligustroside - ≥98% , CAS No.35897-92-8

CAS: 35897-92-8 Cat. No.: L648524 Molecular Weight: 524.51 PubChem CID: 14136859

GRADE & PURITY ≥98%

Synonyms

83S9SA69C5 | Q27269447 | CHEBI:149585 | MS-29709 | 2H-PYRAN-4-ACETIC ACID, 3-ETHYLIDENE-2-(.BETA.-D-GLUCOPYRANOSYLOXY)-3,4-DIHYDRO-5-(METHOXYCARBONYL)-, 2-(4-HYDROXYPHENYL)ETHYL ESTER, (2S,3E,4S)- | AKOS040760521 | DTXSID701318124 | methyl (4S,5E,6S)-5-et

Storage

Store at 2-8°C,Protected from light,Desiccated

Shipped In

Wet ice

Overview

Ligustroside (Ligstroside), a secoiridoid derivative, has outstanding performance on mitochondrial bioenergetics in models of early Alzheimer's disease (AD) and brain ageing by mechanisms that may not interfere with Aβ production. Ligustroside significantly inhibits nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages.

In Vitro

Ligstroside increases mRNA expression of SIRT1, CREB1, complex I, and GPx1 in SH-SY5Y-APP 695 cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Ligstroside (50 mg/kg; a supplemented diet for 6 months) protects against mitochondrial dysfunction in models of early Alzheimer's disease and brain ageing . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Female NMRI mice, aged 12 months Dosage: 50 mg/kg Administration: Received a supplemented diet for 6 months (equivalent to 6.25 mg/kg b.w.) Result: Showed improved spatial working memory; Restored brain ATP levels in aged mice and led to a significant life extension compared to aged control animals.

Form:Solid

Specifications

Synonyms

83S9SA69C5 | Q27269447 | CHEBI:149585 | MS-29709 | 2H-PYRAN-4-ACETIC ACID, 3-ETHYLIDENE-2-(.BETA.-D-GLUCOPYRANOSYLOXY)-3, 4-DIHYDRO-5-(METHOXYCARBONYL)-, 2-(4-HYDROXYPHENYL)ETHYL ESTER, (2S, 3E, 4S)- | AKOS040760521 | DTXSID701318124 | methyl (4S, 5E, 6S)-5-et

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Ligustroside (Ligstroside), a secoiridoid derivative, has outstanding performance on mitochondrial bioenergetics in models of early Alzheimer's disease (AD) and brain ageing by mechanisms that may not interfere with Aβ production. Ligustroside significant

Storage

Store at 2-8°C, Protected from light, Desiccated

Shipped In

Wet ice

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

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC=C(C=C3)O
• IUPAC Name: methyl (4S,5E,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• InChIKey: GMQXOLRKJQWPNB-MVVLSVRYSA-N
• INCHI: 1S/C25H32O12/c1-3-15-16(10-19(28)34-9-8-13-4-6-14(27)7-5-13)17(23(32)33-2)12-35-24(15)37-25-22(31)21(30)20(29)18(11-26)36-25/h3-7,12,16,18,20-22,24-27,29-31H,8-11H2,1-2H3/b15-3+/t16-,18+,20+,21-,22+,24-,25-/m0/s1
• Isomeric SMILES: C/C=C/1\[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC=C(C=C3)O
• PubChem CID: 14136859
• Molecular Weight: 524.51

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Terpene glycosides
• Alternative Parents: O-glycosyl compounds Tyrosols and derivatives Aromatic monoterpenoids Iridoids and derivatives Monocyclic monoterpenoids 1-hydroxy-2-unsubstituted benzenoids Sugar acids and derivatives Benzene and substituted derivatives Dicarboxylic acids and derivatives Monosaccharides Oxanes Methyl esters Enoate esters Vinylogous esters Secondary alcohols Polyols Acetals Oxacyclic compounds Primary alcohols Hydrocarbon derivatives Carbonyl compounds Organic oxides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Terpene glycoside - Glycosyl compound - Secoiridoid-skeleton - O-glycosyl compound - Aromatic monoterpenoid - Monocyclic monoterpenoid - Monoterpenoid - Tyrosol derivative - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Sugar acid - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Monosaccharide - Oxane - Benzenoid - Methyl ester - Enoate ester - Vinylogous ester - Alpha,beta-unsaturated carboxylic ester - Secondary alcohol - Carboxylic acid ester - Polyol - Acetal - Organoheterocyclic compound - Oxacycle - Carboxylic acid derivative - Organic oxygen compound - Alcohol - Organic oxide - Carbonyl group - Primary alcohol - Hydrocarbon derivative - Organooxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.
• External Descriptors: Not available

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

Associated Targets(Human)

SK-BR-3 (5175 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

3T3-L1 (3664 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Flash Point(°F): Not applicable
• Flash Point(°C): Not applicable
• Molecular Weight: 524.500 g/mol
• XLogP3: -0.100
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 11
• Exact Mass: 524.189 Da
• Monoisotopic Mass: 524.189 Da
• Topological Polar Surface Area: 181.000 Ų
• Heavy Atom Count: 37
• Formal Charge: 0
• Complexity: 834.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1