130233-83-9

Basic information

• Product Name: Acerogenin G
• Synonyms: Acerogenin G
• CAS NO: 130233-83-9
• Molecular Formula: C₁₉H₂₂O₃
• Molecular Weight: 298.37618
• Mol File: 130233-83-9.mol

Chemical Properties

• Boiling Point: 526.7±40.0 °C(Predicted)
• Appearance: /
• Density: 1.149±0.06 g/cm3(Predicted)
• Storage Temp.: ?20°C
• PKA: 9.98±0.15(Predicted)
• CAS DataBase Reference: Acerogenin G(CAS DataBase Reference)
• NIST Chemistry Reference: Acerogenin G(130233-83-9)
• EPA Substance Registry System: Acerogenin G(130233-83-9)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 130233-83-9(Hazardous Substances Data)

Upstream product

• 30359-01-4 (3R)-1,7-bis(4'-hydroxyphenyl)-3-heptanol 
• 36603-49-3 4-(tetrahydropyran-2'-yloxy)-1-bromobenzene 
• 106-41-2 4-bromo-phenol 
• 121-98-2 methyl 4-methoxybenzoate 
• 99-96-7 4-hydroxy-benzoic acid 
• 105-13-5 4-Methoxybenzyl alcohol 
• 7400-08-0 p-Coumaric Acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 1083200-79-6 (E)-1,7-bis(4-hydroxyphenyl)hept-1-en-3-one 
• 24807-40-7 methyl 3-(4-benzyloxyphenyl)propanoate 
• 84184-57-6 (E)-3-[4-(methoxymethoxy)phenyl]acrylaldehyde 
• 84184-56-5 (E)-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-ol 
• 74882-26-1 1,7-bis-(4-methoxyphenyl)-heptan-3-one 

Relevant articles and documents

Bio-inspired oxidative phenolic coupling: Total synthesis of the diarylether heptanoid (±)-pterocarine

The diaryletherheptanoid natural product, pterocarine, is expeditiously synthesized using a bioinspired intramolecular oxidative phenolic coupling of acerogenin G. The cyclization precursor is prepared from a simple cinnamic acid derivative in three high yielding synthetic operations. The key oxidative coupling is inspired by biosynthetic hypotheses; however, the oxidative coupling proceeds with concomitant hydroxylation of the diphenyl ether motif.

Synthesis of natural and non-natural curcuminoids and their neuroprotective activity against glutamate-induced oxidative stress in HT-22 cells

A strategy for the synthesis of natural and non-natural 5-deoxy-6,7-dihydrocurcuminoids (diarylheptanoids) was developed for the preparation of 14 compounds with varying aromatic substituent patterns and a different functionality in the aliphatic seven-carbon chain. The in vitro protective activity against glutamate-induced neuronal cell death was examined in the murine hippocampal cell line HT-22 to find structural motifs responsible for neuroprotective effects in vitro. Among the tested compounds the ferulic acid-like unit, present in the structures of (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-en-3-one (5) and (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hept-1-en-3-one (7), appeared to be an important feature for protection against glutamate-induced neurotoxicity. Both compounds demonstrated significant neuroprotective activity in a concentration range between 1 and 25 ～M without showing toxic effects in a cytotoxicity assay with HT-22 cells. Furthermore, (E)-1,7-bis(3,4-dihydroxyphenyl)hept-1-en-3-one (9), exhibiting a caffeic acid-like structural motif, displayed a neuroprotective activity at a nontoxic concentration of 25 ～M. In contrast, (1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione (4, di-O-demethylcurcumin) showed mainly cytotoxic effects. A corresponding single-ring analogue that contains the ferulic acid-like unit as an enone was not active.

Total synthesis of acerogenins E, G and K, and centrolobol

The first total synthesis of the diarylheptanoid acerogenins E and K, isolated from Acer nikoense MAXIM., is described. Formation of the 13-membered m,m-cyclophane skeleton was successfully achieved on the basis of a domino process involving a Miyaura arylborylation-intramolecular Suzuki reaction. The cyclization precursor was prepared via a Wittig reaction and Claisen-Schmidt condensation, which proceeded in moderate yields. The total synthesis of acerogenin G and centrolobol was also achieved from a common synthetic intermediate.

Identification of centrolobol as the platyphylloside metabolite responsible for the observed effect on in vitro digestibility of hay

Syntheses of the metabolites from platyphylloside, a phenol causing digestibility inhibition in rumen fluid, have been performed to identify the active metabolite. 1,7-Bis(4′-hydroxyphenyl)-3-heptanone (3-platyphyllone), racemic, and the two enantiomers o