Loganin - ≥98% , CAS No.18524-94-2

CAS: 18524-94-2 Cat. No.: L111134 分子式: C₁₇H₂₆O₁₀ 分子量: 390.38 Beilstein Registry Number: 55724 EC番号: 242-398-0

GRADE & PURITY ≥98%

Synonyms

(1S,4aS,6S,7R,7aS)-Methyl 6-hydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate | Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

同義語

(1S,4aS,6S,7R,7aS)-Methyl 6-hydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate | Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-

仕様と純度

≥98%

生化学的・生理学的メカニズム

Antioxidant agent. Cytochrome P450 substrate. Shows potent free-radical-scavenging activity. Selective β-secretase inhibitor. COX-1 inhibitor. Shows neuroprotective effects against Aβ(25-35)-induced and hydrogen peroxide-induced cell death.

保管条件

Store at 2-8°C

入荷

Wet ice

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

注

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.

純度

≥98%

名前と識別子

• パブケム・シド: 504755897
• パブケム・シド・ウル: https://pubchem.ncbi.nlm.nih.gov/substance/504755897
• カノニカル・スマイル: CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O
• IUPAC Name: methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• InChIKey: AMBQHHVBBHTQBF-UOUCRYGSSA-N
• INCHI: 1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1
• 異性体SMILES: C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• WGKドイツ: 3
• 分子量: 390.38
• Beilstein: 55724
• Reaxy-Rn: 21050880
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=21050880&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• 分類: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Iridoid O-glycosides
• Alternative Parents: Hexoses O-glycosyl compounds Bicyclic monoterpenoids Iridoids and derivatives Oxanes Vinylogous esters Enoate esters Methyl esters Secondary alcohols Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Acetals Polyols Oxacyclic compounds Carbonyl compounds Primary alcohols Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Iridoid o-glycoside - Hexose monosaccharide - Glycosyl compound - Iridoid-skeleton - O-glycosyl compound - Bicyclic monoterpenoid - Monoterpenoid - Monosaccharide - Oxane - Cyclic alcohol - Vinylogous ester - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Methyl ester - Carboxylic acid ester - Secondary alcohol - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Oxacycle - Acetal - Carboxylic acid derivative - Polyol - Organooxygen compound - Alcohol - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Primary alcohol - Carbonyl group - Aliphatic heteropolycyclic compound
• 説明: This compound belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.
• External Descriptors: Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids

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

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作用メカニズム

化学的性質と物理的性質

• 溶解度: Solubility in water: Completely soluble; Insoluble in Acetone,Chloroform,Ether
• 比旋光度［α］: -84.0 to -87.0 deg(C=0.1, MeOH)
• 融点（°C）: 223.0-227.0℃
• 分子量: 390.400 g/mol
• XLogP3: -1.400
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 390.153 Da
• Monoisotopic Mass: 390.153 Da
• Topological Polar Surface Area: 155.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 580.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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

参考文献

1. Hao Xiaolong, Xie Chenhong, Ruan Qingyan, Zhang Xichen, Wu Chao, Han Bing, Qian Jun, Zhou Wei, Nützmann Hans-Wilhelm, Kai Guoyin.  (2021)  The transcription factor OpWRKY2 positively regulates the biosynthesis of the anticancer drug camptothecin in Ophiorrhiza pumila.  Horticulture Research,      [PMID:33384421] [10.1038/s41438-020-00437-3]