504-15-4 Usage
Description
Orcinol, also known as 5-methylphenol, is an organic compound with the chemical formula C7H8O. It is a white crystalline solid that is soluble in water and has a characteristic aromatic smell. Orcinol is commonly used as a chemical intermediate and reagent in various industrial applications.
Uses
Orcinol is used in the synthesis of various compounds for different applications across various industries. Some of its uses are as follows:
Used in Optical Amplifiers and Light-Emitting Devices:
Orcinol is used as a precursor to synthesize Orcinol-containing azacryptands, which are employed in the development of optical amplifiers and light-emitting devices. These azacryptands exhibit unique properties that make them suitable for use in these high-tech applications.
Used in Crystalline Chemistry:
Orcinol is used to form a ternary co-crystal with 4,4′-bipyridine. This co-crystal exhibits interesting properties and has potential applications in various fields, including materials science and supramolecular chemistry.
Used in the Production of Low-Density Carbon Aerogels:
Orcinol is used in the synthesis of low-density carbon aerogels in the presence of formaldehyde. These aerogels have unique properties, such as high porosity and low density, making them suitable for various applications, including energy storage, catalysis, and environmental remediation.
Used in Cosmetics and Skincare Industry:
Orcinol is used in the synthesis of PEG-orcinol coumarins, which have potent tyrosinase inhibitory activity. Tyrosinase is an enzyme involved in the production of melanin, the pigment responsible for skin color. By inhibiting tyrosinase activity, PEG-orcinol coumarins can help reduce melanin production and are used in cosmetics and skincare products for their skin-lightening properties.
Preparation
Orcinol has been isolated from numerous lichen fungi (Robiquet, 1829) and can be synthesized by decarboxylation of orsellinic acid in Umbilicaria papulosa and Gliocladium roseum (Pettersson, 1965; Mosbach and Ehrensvard, 1966).Orcinol was first prepared by dehydroacetic acid, a conversion that involved ring-opening of the pyrone to a triketone. This early experiment helped establish the rich condensation chemistry of polyketides. It can be obtained by fusing extract of aloes with potash, followed by acidification.US3865884A: Preparation of orcinol
Biological Activity
Orcinol is a compound obtained from DHA which can mimic the biogenetic synthesis of phenolic compounds.Orcinol is a polyketide synthase-derived phenol that has been found in F. graminearum and has diverse biological activities. It scavenges DPPH radicals (IC50 = 2.93 mM). Orcinol (2.5 and 5 mg/kg) increases the number of entries into and percentage of time spent in the open arms of the elevated plus maze in mice, indicating anxiolytic-like activity. It has also been used in the colorimetric detection of carbohydrates.
Safety Profile
Poison by
subcutaneous and intravenous routes.
Moderately toxic by ingestion and
intraperitoneal routes. Mildly toxic by skin
contact. When heated to decomposition it
emits acrid smoke and irritating fumes.
Purification Methods
Crystallise orcinol from CHCl3/*benzene (2:3). See hydrate in previous entry. [Beilstein 6 H 882, 6 IV 5892.]
Check Digit Verification of cas no
The CAS Registry Mumber 504-15-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 4 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 504-15:
(5*5)+(4*0)+(3*4)+(2*1)+(1*5)=44
44 % 10 = 4
So 504-15-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O2/c1-5-2-6(8)4-7(9)3-5/h2-4,8-9H,1H3
504-15-4Relevant articles and documents
Bram,C.
, p. 4069 - 4072 (1967)
COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING SWEET TASTE
-
Paragraph 0358; 0360, (2021/09/17)
The present disclosure provides edible compositions comprising a flavor-grade sweet taste modulator or a combination of flavor-grade sweet taste modulators or a flavor-grade bitter taste blocker or a combination of flavor-grade bitter taste blockers of the present disclosure, food products comprising such edible compositions and methods of preparing such food products. The present disclosure also provides methods of reducing the amount of sugar in a food product, methods of reducing the caloric intake in a diet, and methods of enhancing sweet taste or blocking a bitter taste in a food product.
Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis
Maeda, Katsumi,Matsubara, Ryosuke,Hayashi, Masahiko
supporting information, p. 1530 - 1534 (2021/03/08)
The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.
Mechanism and Structure of γ-Resorcylate Decarboxylase
Sheng, Xiang,Patskovsky, Yury,Vladimirova, Anna,Bonanno, Jeffrey B.,Almo, Steven C.,Himo, Fahmi,Raushel, Frank M.
, p. 3167 - 3175 (2018/06/11)
γ-Resorcylate decarboxylase (γ-RSD) has evolved to catalyze the reversible decarboxylation of 2,6-dihydroxybenzoate to resorcinol in a nonoxidative fashion. This enzyme is of significant interest because of its potential for the production of γ-resorcylate and other benzoic acid derivatives under environmentally sustainable conditions. Kinetic constants for the decarboxylation of 2,6-dihydroxybenzoate catalyzed by γ-RSD from Polaromonas sp. JS666 are reported, and the enzyme is shown to be active with 2,3-dihydroxybenzoate, 2,4,6-trihydroxybenzoate, and 2,6-dihydroxy-4-methylbenzoate. The three-dimensional structure of γ-RSD with the inhibitor 2-nitroresorcinol (2-NR) bound in the active site is reported. 2-NR is directly ligated to a Mn2+ bound in the active site, and the nitro substituent of the inhibitor is tilted significantly from the plane of the phenyl ring. The inhibitor exhibits a binding mode different from that of the substrate bound in the previously determined structure of γ-RSD from Rhizobium sp. MTP-10005. On the basis of the crystal structure of the enzyme from Polaromonas sp. JS666, complementary density functional calculations were performed to investigate the reaction mechanism. In the proposed reaction mechanism, γ-RSD binds 2,6-dihydroxybenzoate by direct coordination of the active site manganese ion to the carboxylate anion of the substrate and one of the adjacent phenolic oxygens. The enzyme subsequently catalyzes the transfer of a proton to C1 of γ-resorcylate prior to the actual decarboxylation step. The reaction mechanism proposed previously, based on the structure of γ-RSD from Rhizobium sp. MTP-10005, is shown to be associated with high energies and thus less likely to be correct.