IUPAC/Chemical Name
2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(10-pentadecenyl)-, (Z)-
InChi Key
WVHQJXPRVZBEFP-SREVYHEPSA-N
InChi Code
InChI=1S/C22H34O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-21(24)19(23)17-20(26-2)22(18)25/h6-7,17,24H,3-5,8-16H2,1-2H3/b7-6-
SMILES Code
O=C1C(O)=C(CCCCCCCCC/C=C\CCCC)C(C(OC)=C1)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
362.51
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Haraguchi H, Ohmi I, Kubo I. Inhibition of aldose reductase by maesanin and related p-benzoquinone derivatives and effects on other enzymes. Bioorg Med Chem. 1996 Jan;4(1):49-53. PubMed PMID: 8689238.
2: Abourashed EA, Muhammad I, Resch M, Bauer R, el-Feraly FS, Hufford CD. Inhibitory effects of maesanin and analogs on arachidonic acid metabolizing enzymes. Planta Med. 2001 Jun;67(4):360-1. PubMed PMID: 11458456.
3: Abourashed EA, el-Feraly FS, Khan IA, Hufford CD. 2-Hydroxy-5-(ethanolamino)-3-(10'-Z-pentadecenyl)-1,4-benzoquinone, new microbial phase II metabolite of maesanin. Chem Pharm Bull (Tokyo). 2000 Jan;48(1):45-7. PubMed PMID: 10705473.
4: Abourashed EA, El-Feraly FS, Hufford CD. Carboxylic acid microbial metabolites of the natural benzoquinone, maesanin . J Nat Prod. 1999 May;62(5):714-6. PubMed PMID: 10346952.
5: Fukuyama Y, Kiriyama Y, Okino J, Kodama M, Iwaki H, Hosozawa S, Matsui K. Naturally occurring 5-lipoxygenase inhibitor. II. Structures and syntheses of ardisianones A and B, and maesanin, alkenyl-1,4-benzoquinones from the rhizome of Ardisia japonica. Chem Pharm Bull (Tokyo). 1993 Mar;41(3):561-5. PubMed PMID: 8477510.
6: Abourashed EA, El-Feraly FS, Hufford CD. Carboxylic acid microbial metabolites of the natural benzoquinone, maesanin. J Nat Prod. 1999 Oct;62(10):1474. PubMed PMID: 10545055.
7: Makawiti DW, Konji VN, Olowookere JO. Interaction of benzoquinones with mitochondria interferes with oxidative phosphorylation characteristics. FEBS Lett. 1990 Jun 18;266(1-2):26-8. PubMed PMID: 2365068.
8: Muhammad I, Takamatsu S, Walker LA, Mossa JS, Fong HH, El-Feraly FS. Cytotoxic and antioxidant activities of alkylated benzoquinones from Maesa lanceolata. Phytother Res. 2003 Sep;17(8):887-91. PubMed PMID: 13680818.
9: Li YF, Li J, Shen Q, Hu LH. Benzoquinones from Ardisia japonica with inhibitory activity towards human protein tyrosine phosphatase 1B (PTP1B). Chem Biodivers. 2007 May;4(5):961-5. PubMed PMID: 17511011.
