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MedKoo Cat#: 573238 | Name: Deoxyshikonin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Deoxyshikonin is a drug which may elevate tube formation in HUVECs and induce proliferation and migration in HaCaT cells . Collectively, these data suggest that deoxyshikonin must be an active compound for may be wound healing.

Chemical Structure

Deoxyshikonin
Deoxyshikonin
CAS#43043-74-9

Theoretical Analysis

MedKoo Cat#: 573238

Name: Deoxyshikonin

CAS#: 43043-74-9

Chemical Formula: C16H16O4

Exact Mass: 272.1049

Molecular Weight: 272.30

Elemental Analysis: C, 70.58; H, 5.92; O, 23.50

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Arnebin 7, Deoxyshikonin
IUPAC/Chemical Name
1,4-Naphthalenedione, 5,8-dihydroxy-2-(4-methyl-3-pentenyl)-
InChi Key
VOMDIEGPEURZJO-UHFFFAOYSA-N
InChi Code
1S/C16H16O4/c1-9(2)4-3-5-10-8-13(19)14-11(17)6-7-12(18)15(14)16(10)20/h4,6-8,17-18H,3,5H2,1-2H3
SMILES Code
CC(=CCCC1=CC(=O)c2c(ccc(c2C1=O)O)O)C
Appearance
Solid powder
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 272.30 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.

Recalculate based on batch purity %
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: Orejarena Pacheco JC, Lahm G, Opatz T. Synthesis of alkaloids by Stevens rearrangement of nitrile-stabilized ammonium ylides: (±)-laudanosine, (±)-laudanidine, (±)-armepavine, (±)-7-methoxycryptopleurine, and (±)-xylopinine. J Org Chem. 2013 May 17;78(10):4985-92. doi: 10.1021/jo400659n. Epub 2013 May 9. PubMed PMID: 23634947. 2: Weng TC, Shen CC, Chiu YT, Lin YL, Huang YT. Effects of armepavine against hepatic fibrosis induced by thioacetamide in rats. Phytother Res. 2012 Mar;26(3):344-53. doi: 10.1002/ptr.3539. Epub 2011 Jun 30. PubMed PMID: 21717514. 3: Weng TC, Shen CC, Chiu YT, Lin YL, Kuo CD, Huang YT. Inhibitory effects of armepavine against hepatic fibrosis in rats. J Biomed Sci. 2009 Sep 2;16:78. doi: 10.1186/1423-0127-16-78. PubMed PMID: 19723340; PubMed Central PMCID: PMC2741443. 1: Park JY, Shin MS, Hwang GS, Yamabe N, Yoo JE, Kang KS, Kim JC, Lee JG, Ham J, Lee HL. Beneficial Effects of Deoxyshikonin on Delayed Wound Healing in Diabetic Mice. Int J Mol Sci. 2018 Nov 20;19(11). pii: E3660. doi: 10.3390/ijms19113660. PubMed PMID: 30463303; PubMed Central PMCID: PMC6274849. 2: Vukic MD, Vukovic NL, Djelic GT, Popovic SL, Zaric MM, Baskic DD, Krstic GB, Tesevic VV, Kacaniova MM. Antibacterial and cytotoxic activities of naphthoquinone pigments from Onosma visianii Clem. EXCLI J. 2017 Feb 16;16:73-88. doi: 10.17179/excli2016-762. eCollection 2017. PubMed PMID: 28435429; PubMed Central PMCID: PMC5379117. 3: Park JY, Kwak JH, Kang KS, Jung EB, Lee DS, Lee S, Jung Y, Kim KH, Hwang GS, Lee HL, Yamabe N, Kim SN. Wound healing effects of deoxyshikonin isolated from Jawoongo: In vitro and in vivo studies. J Ethnopharmacol. 2017 Mar 6;199:128-137. doi: 10.1016/j.jep.2016.10.031. Epub 2016 Oct 8. PubMed PMID: 27725239. 4: Zhang S, Wang J, Xu W, Liu Y, Wang W, Wu K, Wang Z, Zhang X. Antibacterial effects of Traditional Chinese Medicine monomers against Streptococcus pneumoniae via inhibiting pneumococcal histidine kinase (VicK). Front Microbiol. 2015 May 20;6:479. doi: 10.3389/fmicb.2015.00479. eCollection 2015. PubMed PMID: 26042111; PubMed Central PMCID: PMC4438233. 5: Zhao Q, Kretschmer N, Bauer R, Efferth T. Shikonin and its derivatives inhibit the epidermal growth factor receptor signaling and synergistically kill glioblastoma cells in combination with erlotinib. Int J Cancer. 2015 Sep 15;137(6):1446-56. doi: 10.1002/ijc.29483. Epub 2015 Mar 6. PubMed PMID: 25688715. 6: Prangsaengtong O, Park JY, Inujima A, Igarashi Y, Shibahara N, Koizumi K. Enhancement of Lymphangiogenesis In Vitro via the Regulations of HIF-1α Expression and Nuclear Translocation by Deoxyshikonin. Evid Based Complement Alternat Med. 2013;2013:148297. doi: 10.1155/2013/148297. Epub 2013 Apr 22. PubMed PMID: 23737816; PubMed Central PMCID: PMC3664343.