Avarol

AdipoGen Life Sciences
Product Code: AG-CN2-0044
CodeSizePrice
AG-CN2-0044-M0011 mg£130.00
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Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient

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Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
NSC 306951
Appearance:
Off-white solid.
CAS:
55303-98-5
EClass:
32160000
Form (Short):
solid
Handling Advice:
Keep cool and dry.Protect from light.
InChi:
InChI=1S/C21H30O2/c1-14-6-5-7-19-20(14,3)11-10-15(2)21(19,4)13-16-12-17(22)8-9-18(16)23/h6,8-9,12,15,19,22-23H,5,7,10-11,13H2,1-4H3/t15-,19+,20+,21+/m0/s1
InChiKey:
JSPUCPNQXKTYRO-LWILDLIXSA-N
Long Description:
Chemical. CAS: 55303-98-5. Formula: C21H30O2. MW: 314.5. Isolated from sponge Dysidea avara. Antibacterial against selected Gram-positive strains, antifungal. Anticancer compound. Antileukemic. Antimitotic agent. Antiviral compound. Inhibits HIV activity. Anti-inflammatory. Synovial phospholipase A2, cyclooxygenase and lipoxygenase inhibitor. Modulator of superoxide dismutase and glutathione peroxidase. Platelet aggregation inhibitor. Anti-psoriatic, mediated by inhibition of TNF-alpha generation and NF-kappaB activation. Reviews.
MDL:
MFCD01657132
Molecular Formula:
C21H30O2
Molecular Weight:
314.5
Package Type:
Vial
Product Description:
Antibacterial against selected Gram-positive strains, antifungal [1, 6]. Anticancer compound [2]. Antileukemic [4, 5, 8, 9]. Antimitotic agent [3]. Antiviral compound [7, 8, 14]. Inhibits HIV activity [7, 8, 14]. Anti-inflammatory [10, 12]. Synovial phospholipase A2, cyclooxygenase and lipoxygenase inhibitor [10, 12]. Modulator of superoxide dismutase and glutathione peroxidase [11]. Platelet aggregation inhibitor [13]. Anti-psoriatic [15, 17], mediated by inhibition of TNF-alpha generation and NF-kappaB activation [18, 19]. Reviews [16, 20].
Purity:
>97% (HPLC)
SMILES:
[H][C@@]12CCC=C(C)[C@@]1(C)CC[C@H](C)[C@@]2(C)CC1=CC(O)=CC=C1O
Solubility Chemicals:
Soluble in ethanol or DMSO.
Source / Host:
Isolated from sponge Dysidea avara.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C. Store solutions at -20°C in the dark.

References

Antimicrobial activity of avarol, a sesquiterpenoid hydroquinone from the marine sponge, Dysidea avara: L. Cariello, et al.; Comp. Biochem. Physiol. B. 71, 281 (1982) | Avarol, a cytostatically active compound from the marine sponge Dysidea avara: W.E. M?ller, et al.; Comp. Biochem. Physiol. C. 80, 47 (1985) | Inhibition of mitosis by avarol, a natural product isolated from the sponge Dysidea avara: W.E. M?ller, et al.; Basic Appl. Histochem. 29, 321 (1985) | Potent antileukemic activity of the novel cytostatic agent avarone and its analogues in vitro and in vivo: W.E. M?ller, et al.; Cancer Res. 45, 4822 (1985) | Antimutagenic activity of the novel antileukemic agents, avarone and avarol: B. Kurelec, et al.; Mutat. Res. 144, 63 (1985) | Antibacterial and antifungal activity of Avarone and Avarol: G. Seibert, et al.; Zentralbl. Bakteriol. Mikrobiol. Hyg. A. 260, 379 (1985) | Inhibition of replication of the etiologic agent of acquired immune deficiency syndrome (human T-lymphotropic retrovirus/lymphadenopathy-associated virus) by avarol and avarone: P.S. Sarin, et al.; J. Natl. Cancer Inst. 78, 663 (1987) | Influence of the antileukemic and anti-human immunodeficiency virus agent avarol on selected immune responses in vitro and in vivo: W.E. M?ller, et al.; Biochem. Pharmacol. 36, 1489 (1987) | Avarol-induced DNA strand breakage in vitro and in Friend erythroleukemia cells: W.E. M?ller, et al.; Cancer Res. 47, 6565 (1987) | Induction of gamma-interferon by avarol in human peripheral blood lymphocytes: R. Voth, et al.; Jpn. J. Cancer Res. 79, 647 (1988) | Action of the antileukemic and anti-HTLV-III (anti-HIV) agent avarol on the levels of superoxide dismutases and glutathione peroxidase activities in L5178y mouse lymphoma cells: E. Batke, et al.; Cell Biochem. Funct. 6, 123 (1988) | Avarol and avarone, two new anti-inflammatory agents of marine origin: M.L. Ferrandiz, et al.; Eur. J. Pharmacol. 253, 75 (1994) | In vitro effect of avarone and avarol, a quinone/hydroquinone couple of marine origin, on platelet aggregation: M.A. Belisario, et al.; Pharmacol. Toxicol. 79, 300 (1996) | Natural products with anti-HIV activity from marine organisms: L.A. Tziveleka, et al.; Curr. Top. Med. Chem. 3, 1512 (2003) (Review) | Potential antipsoriatic avarol derivatives as antioxidants and inhibitors of PGE(2) generation and proliferation in the HaCaT cell line: M. Amigo, et al.; J. Nat. Prod. 67, 1459 (2004) | Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order Dictyoceratida: D. Sladic & M.J. Gasic; Molecules 11, 1 (2006) | Identification of avarol derivatives as potential antipsoriatic drugs using an in vitro model for keratinocyte growth and differentiation: M. Amig?, et al.; Life Sci. 79, 2395 (2006) | Antipsoriatic effects of avarol-3'-thiosalicylate are mediated by inhibition of TNF-alpha generation and NF-kappaB activation in mouse skin: M Amig?, et al.; Br. J. Pharmacol. 152, 353 (2007) | Avarol inhibits TNF-alpha generation and NF-kappaB activation in human cells and in animal models: M. Amig?, et al.; Life Sci. 82, 256 (2008) | Cytotoxic terpene quinones from marine sponges: M. Gordaliza; Mar. Drugs 8, 2849 (2010) | Avarol induces apoptosis in pancreatic ductal adenocarcinoma cells by activating PERK?eIF2alpha?CHOP signaling: T. Namba & R. Kodama; Mar. Drugs 13, 2376 (2015)