Loganic acid

Base Information

• Chemical Name: Loganic acid
• CAS No.: 22255-40-9
• Molecular Formula: C₁₆H₂₄O₁₀
• Molecular Weight: 376.361
• European Community (EC) Number: 244-875-9
• UNII: UX3J3KK2UG
• DSSTox Substance ID: DTXSID80944913
• Nikkaji Number: J15.893C
• Wikipedia: Loganic_acid
• Wikidata: Q19597767
• Metabolomics Workbench ID: 52009
• ChEMBL ID: CHEMBL1081585
• Mol file: 22255-40-9.mol

Synonyms:8-epiloganic acid;loganic acid

Chemical Property of Loganic acid

Chemical Property:

• Vapor Pressure: 1.97E-19mmHg at 25°C
• Refractive Index: 1.633
• Boiling Point: 646.257 °C at 760 mmHg
• PKA: 4.55±0.70(Predicted)
• Flash Point: 235.557 °C
• PSA: 166.14000
• Density: 1.6 g/cm³
• LogP: -2.23920
• Storage Temp.: ?20°C
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 376.13694696
• Heavy Atom Count: 26
• Complexity: 565

Purity/Quality:

≥98% ^*data from raw suppliers

Loganic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• General Description: Loganic acid is a monoterpene glucoside that serves as a key intermediate in the biosynthesis of iridoids, secoiridoids, and potentially indole alkaloids. It is derived from mevalonate via geranyl pyrophosphate and plays a crucial role in the formation of compounds like gentiopicroside through ring cleavage. Its structure includes a cyclopenta[c]pyran core with a β-D-glucopyranosyloxy substituent, a hydroxy group, and a methyl group, confirming its mevalonoid origin and its significance in plant secondary metabolism.

Technology Process of Loganic acid

There total 11 articles about Loganic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1S,4aS,6S,7R,7aS)-7-Methyl-6-[(E)-(3-phenyl-acryloyl)oxy]-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid (79636-20-7) → (E)-3-phenylacrylic acid (140-10-3) + loganic acid (82509-41-9,22255-40-9)

Guidance literature:

With sodium hydroxide; Ambient temperature;

Reference yield:

methanol (67-56-1) + 2'-(2'',3''-dihydroxybenzoyl)loganic acid → methyl-2,3-dihydroxybenzoate (2411-83-8) + loganic acid (82509-41-9,22255-40-9)

Guidance literature:

With sodium hydroxide; at 30 ℃; for 3h;

DOI:10.1007/s10600-016-1728-y

Reference yield:

bis-desoxy-dihydro-monotropein (22487-36-1) → loganic acid (82509-41-9,22255-40-9)

Guidance literature:

With NADPH; 7-deoxyloganin 7-hydroxylase; In water; at 30 ℃; for 0.166667h; pH=7.5;

DOI:10.1016/S0031-9422(01)00181-9

upstream raw materials:

Ligustrinoside

loganin

(1S,4aS,6S,7R,7aS)-7-Methyl-6-[(E)-(3-phenyl-acryloyl)oxy]-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid

bis-desoxy-dihydro-monotropein

Downstream raw materials:

loganin

alyxialactone

4-epi-Alyxialactone

2',3',4',6',7-penta-O-acetylloganin

Refernces

Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis

10.1021/bi00840a054

The research investigates the biosynthesis of gentiopicroside and loganic acid, two monoterpene glucosides found in the plant Swertia caroliniensis. The study aims to elucidate their biosynthetic pathways and confirm their mevalonoid origin. Key chemicals used include acetate-2-14C, mevalonate-2-14C, and mevalonate-2-3H-2-14C as labeled precursors. Through tracer experiments and various chemical transformations such as methylation, acetylation, and oxidation, the researchers demonstrated that both compounds originate from mevalonate. They also revised the structure of gentiopicroside based on chemical and spectral data, including double-resonance nuclear magnetic resonance studies. The results support a biogenetic scheme where mevalonate is converted to geranyl pyrophosphate, then to loganic acid, which undergoes ring cleavage to form gentiopicroside. The study concludes that loganic acid and its derivatives play a significant role as precursors for various iridoids and secoiridoids, and potentially for indole alkaloids, highlighting the interconnected biosynthetic pathways of these plant metabolites.

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