Spinulosin
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| Category | Antibiotics |
| Catalog number | BBF-03459 |
| CAS | 85-23-4 |
| Molecular Weight | 184.15 |
| Molecular Formula | C8H8O5 |
| Purity | 95% |
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Description
It is produced by the strain of Pen. spinulosurn, Pen. cinerascens, Asp. fumigatas. It has anti-bacterial effect, but the effect is not strong.
Specification
| Related CAS | 28068-28-2 (hydrate) |
| Synonyms | 2,5-dihydroxy-3-methyl-6-methoxy-1,4-benzoquinone; 3,6-dihydroxy-5-methoxy-p-toluquinone; 3,6-dihydroxy-4-methoxy-2,5-toluquinone; Hydroxyfumigatin |
| IUPAC Name | 2,5-dihydroxy-3-methoxy-6-methylcyclohexa-2,5-diene-1,4-dione |
| Canonical SMILES | CC1=C(C(=O)C(=C(C1=O)O)OC)O |
| InChI | InChI=1S/C8H8O5/c1-3-4(9)6(11)8(13-2)7(12)5(3)10/h9,12H,1-2H3 |
| InChI Key | GFAZBXKENDSJEB-UHFFFAOYSA-N |
Properties
| Appearance | Purple-black Flaky Crystal |
| Boiling Point | 364.2°C at 760 mmHg |
| Melting Point | 202°C |
| Density | 1.48 g/cm3 |
Reference Reading
1.Effect of 2-dodecyl-6-methoxycyclohexa-2,5-diene-1,4-dione, isolated from Averrhoa carambola L. (Oxalidaceae) roots, on advanced glycation end-product-mediated renal injury in type 2 diabetic KKAy mice.
Zheng N1, Lin X, Wen Q, Kintoko, Zhang S, Huang J, Xu X, Huang R. Toxicol Lett. 2013 May 10;219(1):77-84. doi: 10.1016/j.toxlet.2013.03.001. Epub 2013 Mar 13.
The roots of Averrhoa carambola L. (Oxalidaceae) have a long history of medical use in traditional Chinese medicine for treating diabetes and diabetic nephropathy. 2-Dodecyl-6-methoxycyclohexa-2,5-diene-1,4-dione (DMDD) was isolated from the tuberous roots of A. carambola L. The purpose of this study was to investigate the beneficial effect of DMDD on the advanced glycation end-product-mediated renal injury in type 2 diabetic KKAy mice with regard to prove its efficacy by local traditional practitioners in the treatment of kidney frailties in diabetics. KKAy mice were orally administrated DMDD (12.5, 25, 50mg/kg body weight/d) or aminoguanidine (200mg/kg body weight/d) for 8 weeks. Hyperglycemia, renal AGE formation, and the expression of related proteins, such as the AGE receptor, nuclear factor-κB, transforming growth factor-β1, and N(ε)-(carboxymethyl)lysine, were markedly decreased by DMDD. Diabetes-dependent alterations in proteinuria, serum creatinine, creatinine clearance, and serum urea-N and glomerular mesangial matrix expansion were attenuated after treatment with DMDD for 8 weeks.
2.2,5-Di-bromo-3,6-dimeth-oxycyclo-hexa-2,5-diene-1,4-dione.
Orhan E1, Garci A1, Therrien B1. Acta Crystallogr Sect E Struct Rep Online. 2014 May 24;70(Pt 6):o715. doi: 10.1107/S1600536814011787. eCollection 2014.
In the structure of the title compound, C8H6Br2O4, the complete mol-ecule is generated by the application of a centre of inversion. The mol-ecule is planar (r.m.s. deviation for all non-H atoms but methyl C = 0.0358 Å), with only the methyl groups being deviated from the plane [by ±0.321 (4) Å]. In the crystal packing, Br⋯O(methoxy) halogen bonds [3.2407 (19) Å] connect molecules into supramolecular layers parallel to (101).
3.Cyclohexa-2,5-diene-1,4-dione-based antiproliferative agents: design, synthesis, and cytotoxic evaluation.
Petronzi C1, Festa M, Peduto A, Castellano M, Marinello J, Massa A, Capasso A, Capranico G, La Gatta A, De Rosa M, Caraglia M, Filosa R. J Exp Clin Cancer Res. 2013 Apr 30;32:24. doi: 10.1186/1756-9966-32-24.
BACKGROUND: Tumors are diseases characterized by uncontrolled cell growth and, in spite of the progress of medicine over the years, continue to represent a major threat to the health, requiring new therapies. Several synthetic compounds, such as those derived from natural sources, have been identified as anticancer drugs; among these compounds quinone represent the second largest class of anticancer agents in use. Several studies have shown that these act on tumor cells through several mechanisms. An important objective of this work is to develop quinoidscompounds showing antitumor activity, but with fewer side effects. The parachinone cannabinol HU-331, is a small molecule that with its core 4-hydroxy-1,4-benzoquinone, exhibits a potent and selective cytotoxic activity on different tumor cell lines. A series of derivatives 3-hydroxy-1,4-benzochinoni were thus developed through HU-331 chemical modifications. The purpose of the work is to test the ability of the compounds to induce proliferative inhibition and study the mechanisms of cell death.
4.The antidiabetic compound 2-dodecyl-6-methoxycyclohexa-2,5-diene-1,4-dione, isolated from Averrhoa carambola L., demonstrates significant antitumor potential against human breast cancer cells.
Gao Y1, Huang R2, Gong Y3, Park HS1, Wen Q2, Almosnid NM1, Chippada-Venkata UD3, Hosain NA1, Vick E1, Farone A1, Altman E1. Oncotarget. 2015 Sep 15;6(27):24304-19.
2-Dodecyl-6-methoxycyclohexa-2,5-diene-1,4-dione (DMDD) is a cyclohexanedione found in the roots of Averrhoa carambola L., commonly known as starfruit. Researchers have shown that DMDD has significant therapeutic potential for the treatment of diabetes; however, the effects of DMDD on human cancers have never been reported. We investigated the cytotoxic effects of DMDD against human breast, lung and bone cancer cells in vitro and further examined the molecular mechanisms of DMDD-induced apoptosis in human breast cancer cells. DMDD suppressed the growth of breast carcinoma cells, but not normal mammary epithelial cells, via induction of G1 phase cell cycle arrest, oxidative stress and apoptosis. DMDD increased the level of intracellular reactive oxygen species (ROS) and DMDD-induced ROS generation was found to be associated with the mitochondrial activity. The cytotoxicity that was induced by DMDD was attenuated by co-treatment with the antioxidant N-acetyl-L-cysteine (NAC).
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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 ╳
