480-64-8 Usage
Description
2,4-Dihydroxy-6-methylbenzoic acid, also known as Orsellinic acid, is a benzoic acid derivative and a fungal metabolite with antioxidant and neuroprotective properties. It is characterized by the presence of two hydroxyl groups at the 2nd and 4th positions and a methyl group at the 6th position of the benzene ring. Orsellinic acid has demonstrated its ability to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals and prevent platelet-activating factor (PAF)-induced neuronal apoptosis.
Uses
Used in Pharmaceutical Industry:
2,4-Dihydroxy-6-methylbenzoic acid is used as a neuroprotective agent for its ability to block PAF-mediated neuronal apoptosis. It plays a crucial role in preventing PARP cleavage and cytotoxicity in various cell types, making it a potential candidate for the development of treatments targeting neurodegenerative diseases.
Used in Antioxidant Applications:
As an antioxidant, 2,4-Dihydroxy-6-methylbenzoic acid is used to neutralize free radicals, such as DPPH radicals, with an IC50 value of 5 mM. Its antioxidant properties make it a valuable compound for the development of products aimed at reducing oxidative stress and promoting overall health.
Used in Chemical Synthesis:
Orsellinic acid can be utilized as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, dyes, and other specialty chemicals. Its unique structure and functional groups make it a versatile building block for creating a wide range of molecules with diverse applications.
Biosynthesis
One of the simplest polyketide derivatives, orsellinic acid is widely distributed in fungi. It is biosynthesised from an acetate starter unit and three malonyl units, as shown in Figure. Intramolecular condensation of the polyketide chain gives orsellinic acid without further modification.
The biosynthesis of orsellinic acid.
Synthesis Reference(s)
The Journal of Organic Chemistry, 30, p. 3566, 1965 DOI: 10.1021/jo01021a507
Check Digit Verification of cas no
The CAS Registry Mumber 480-64-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 0 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 480-64:
(5*4)+(4*8)+(3*0)+(2*6)+(1*4)=68
68 % 10 = 8
So 480-64-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12)
480-64-8Relevant articles and documents
An orsellinic acid glucoside from Syzygium aromatica
Charles, Reena,Garg, Shri Niwas,Kumar, Sushil
, p. 1375 - 1376 (1998)
The buds of Syzygium aromatica yielded two triterpenoid acids, oleanolic acid and crategolic acid, and a new phenolic glucoside, orsellinic-2-O-β-D- glucopyranoside, from its methanolic extract. The structure was elucidated by spectroscopic methods and acid hydrolysis.
CRUSTINIC ACID, A TRIDEPSIDE FROM UMBILICARIA CRUSTULOSA
Huneck, S.,Porzel, A.,Schmidt, J.,Feige, G. B.,Posner, B.
, p. 475 - 477 (1993)
The structure of crustinic acid extracted from Umbilicaria crustulosa has been elucidated as 4,6-dihydroxy-3-carboxy-2-methylphenyl lecanorate by spectroscopic and chemical means.Key Word Index - Umbilicaria crustulosa; Umbilicariaceae; crustinic acid; tridepside; lichen substance.
Kolbe-Schmitt type reaction under ambient conditions mediated by an organic base
Sadamitsu, Yuta,Okumura, Akira,Saito, Kodai,Yamada, Tohru
supporting information, p. 9837 - 9840 (2019/08/20)
The combined use of an organic base for resorcinols realized a Kolbe-Schmitt type reaction under ambient conditions. When resorcinols (3-hydroxyphenol derivatives) were treated with DBU under a carbon dioxide atmosphere, nucleophilic addition to carbon dioxide proceeded to afford the corresponding salicylic acid derivatives in high yields.
New orsellinic acid esters from fungus chaetomium globosporum
Xu, Guo-Bo,Wang, Ni-Ni,Bao, Jin-Ku,Yang, Tao,Li, Guo-You
, p. 151 - 159 (2014/02/14)
Seven new orsellinic acid esters, 1-7, and four known compounds were isolated from the solid, fermented rice culture of Chaetomium globosporum (cib-132). Their structures were elucidated by 1D- and 2D-NMR spectra, and the relative configuration of compoun
