Orsellinic acid
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| Category | Others |
| Catalog number | BBF-02624 |
| CAS | 480-64-8 |
| Molecular Weight | 168.15 |
| Molecular Formula | C8H8O4 |
| Purity | 99.0% |
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Description
Orsellinic acid is from Chaetomium globosum endophytic. Orsellinic acid can block platelet activating factor (PAF)-mediated neuronal apoptosis without affecting G-protein coupled receptor (PAFR)-mediated neuroprotection, and it can effectively attenuate PAFR-independent neuronal apoptosis. It is a novel benzoquinone ring precursor for antroquinonol and 4-acetylantroquinonol B. It is formed from acetyl-coenzyme Q (CoQ) and malonyl-CoA via polyketide pathway.
Specification
| Synonyms | o-Orsellinic acid; 4,6-Dihydroxy-o-toluic acid |
| Storage | Store at -20°C |
| IUPAC Name | 2,4-dihydroxy-6-methylbenzoic acid |
| Canonical SMILES | CC1=CC(=CC(=C1C(=O)O)O)O |
| InChI | InChI=1S/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12) |
| InChI Key | AMKYESDOVDKZKV-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Acicular Crystals |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 257.07°C at 760 mmHg |
| Melting Point | 176°C |
| Density | 1.3037 g/cm3 |
| Solubility | Soluble in water, DMSO or 100% ethanol. |
Reference Reading
1.Isolation, characterization and antifungal activity of major constituents of the Himalayan lichen Parmelia reticulata Tayl.
Goel M1, Dureja P, Rani A, Uniyal PL, Laatsch H. J Agric Food Chem. 2011 Mar 23;59(6):2299-307. doi: 10.1021/jf1049613. Epub 2011 Feb 25.
Antifungal activity of hexane, ethyl acetate and methanol extracts of Parmelia reticulata was evaluated against soilborne pathogenic fungi, namely, Sclerotium rolfsii, Rhizoctonia solani, R. bataticola, Fusarium udum, Pythium aphanidermatum and P. debaryanum by poisoned food technique. Maximum antifungal activity was exhibited by hexane and ethyl acetate extracts against most of the test pathogens. Secondary metabolites, namely, (±)-isousnic acid, (±)-protolichesterinic acid, atranorin, evernyl, ethyl hematommate, ethyl orsellinate, methyl hematommate (3-formyl-2,4-dihydroxy-6-methylbenzoic acid methyl ester), 2-hydroxy-4-methoxy-3,6-dimethylbenzoic acid, 1-hydroxy-3,6-dimethoxy-8-methyl-xanthen-9-one, baeomycesic acid and salazinic acid, were isolated from the above extracts and identified by 1H NMR, 13C NMR and mass spectroscopic methods. When these metabolites were tested for antifungal activity against test pathogens, maximum antifungal activity was exhibited by (±)-protolichesterinic acid against R.
2.A short synthetic route to biologically active (+/-)-daurichromenic acid as highly potent anti-HIV agent.
Lee YR1, Wang X. Org Biomol Chem. 2005 Nov 7;3(21):3955-7. Epub 2005 Sep 22.
The efficient total synthesis of biologically interesting (+/-)-daurichromenic acid is accomplished starting from 2,4-dihydroxy-6-methylbenzoic acid or 2,4-dihydroxy-6-methylbenzaldehyde in one or two steps.
3.Polyketides with α-Glucosidase Inhibitory Activity from a Mangrove Endophytic Fungus, Penicillium sp. HN29-3B1.
Liu Y, Yang Q1, Xia G, Huang H, Li H, Ma L, Lu Y, He L, Xia X2, She Z. J Nat Prod. 2015 Aug 28;78(8):1816-22. doi: 10.1021/np500885f. Epub 2015 Jul 31.
Five new compounds, pinazaphilones A and B (1, 2), two phenolic compounds (4, 5), and penicidone D (6), together with the known Sch 1385568 (3), (±)-penifupyrone (7), 3-O-methylfunicone (8), 5-methylbenzene-1,3-diol (9), and 2,4-dihydroxy-6-methylbenzoic acid (10) were obtained from the culture of the endophytic fungus Penicillium sp. HN29-3B1, which was isolated from a fresh branch of the mangrove plant Cerbera manghas collected from the South China Sea. Their structures were determined by analysis of 1D and 2D NMR and mass spectroscopic data. Structures of compounds 4 and 7 were further confirmed by a single-crystal X-ray diffraction experiment using Cu Kα radiation. The absolute configurations of compounds 1-3 were assigned by quantum chemical calculations of the electronic circular dichroic spectra. Compounds 2, 3, 5, and 7 inhibited α-glucosidase with IC50 values of 28.0, 16.6, 2.2, and 14.4 μM, respectively, and are thus more potent than the positive control, acarbose.
4.Cytotoxic activity of orsellinates.
Gomes AT1, Honda NK, Roese FM, Muzzi RM, Sauer L. Z Naturforsch C. 2006 Sep-Oct;61(9-10):653-7.
The series of 2,4-dihydroxy-6-methylbenzoates 2-10 (methyl to hexyl orsellinates) prepared by alcoholysis of lecanoric acid (1)--a natural product from the lichen Parmotrema tinctorum (Nyl.) Hale - was submitted to the brine shrimp lethality test (BST), which was also performed for 2,4-dihydroxy-6-methylbenzoic acid (11) (orsellinic acid) and the derivative ethyl-2-hydroxy-4-methoxy-6-methylbenzoate (12) (4-methoxy-ethyl orsellinate), in order to detect new substances with probable antineoplasic activity. Results showed that chain elongation--increase in lipophilicity (log P)--causes a rise in the cytotoxic activity of orsellinates. Hexyl orsellinate (7) showed the highest cytotoxic activity (LC50 = 31 microM). A correlation between lipophilicity (log P) and cytotoxic activity (log 1/LC50) is presented. Compounds with ramified chains--iso-propyl, sec-butyl and tert-butyl orsellinates (8-10)--were less active than those with the correspondent linear chain.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
