(+-)-Shikonin | CAS# 54952-43-1 | Biochemical

(+-)-Shikonin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 573239

CAS#: 54952-43-1

Description: (+-)-Shikonin is a naphthazarin with antineoplastic and angiogenesis inhibiting activities.

Chemical Structure

(+-)-Shikonin

CAS# 54952-43-1

Instruction

Theoretical Analysis

MedKoo Cat#: 573239
Name: (+-)-Shikonin
CAS#: 54952-43-1
Chemical Formula: C16H16O5
Exact Mass: 288.10
Molecular Weight: 288.300
Elemental Analysis: C, 66.66; H, 5.59; O, 27.75

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 265
50mg	USD 755
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: (+-)-Alkannin, (+-)-Shikonin, Arnebin-4, Shikonin

IUPAC/Chemical Name: 1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)- (9CI)

InChi Key: NEZONWMXZKDMKF-UHFFFAOYSA-N

InChi Code: 1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3

SMILES Code: CC(=CCC(C1=CC(=O)c2c(ccc(c2C1=O)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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 288.30 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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Qiu HY, Fu JY, Yang MK, Han HW, Wang PF, Zhang YH, Lin HY, Tang CY, Qi JL, Yang RW, Wang XM, Zhu HL, Yang YH. Identification of new shikonin derivatives as STAT3 inhibitors. Biochem Pharmacol. 2017 Dec 15;146:74-86. doi: 10.1016/j.bcp.2017.10.009. Epub 2017 Oct 21. PubMed PMID: 29066190.

2: Zhai T, Hei Z, Ma Q, Liang H, Xu Y, Zhang Y, Jin L, Han C, Wang J. Shikonin induces apoptosis and G0/G1 phase arrest of gallbladder cancer cells via the JNK signaling pathway. Oncol Rep. 2017 Dec;38(6):3473-3480. doi: 10.3892/or.2017.6038. Epub 2017 Oct 17. PubMed PMID: 29039581.

3: Lu B, Gong X, Wang ZQ, Ding Y, Wang C, Luo TF, Piao MH, Meng FK, Chi GF, Luo YN, Ge PF. Shikonin induces glioma cell necroptosis in vitro by ROS overproduction and promoting RIP1/RIP3 necrosome formation. Acta Pharmacol Sin. 2017 Nov;38(11):1543-1553. doi: 10.1038/aps.2017.112. Epub 2017 Aug 17. PubMed PMID: 28816233; PubMed Central PMCID: PMC5672068.

4: Yang J, Wang Z, Chen DL. Shikonin ameliorates isoproterenol (ISO)-induced myocardial damage through suppressing fibrosis, inflammation, apoptosis and ER stress. Biomed Pharmacother. 2017 Sep;93:1343-1357. doi: 10.1016/j.biopha.2017.06.086. Epub 2017 Jul 24. PubMed PMID: 28753907.

5: Zhou G, Yang Z, Wang X, Tao R, Zhou Y. TRAIL Enhances Shikonin Induced Apoptosis through ROS/JNK Signaling in Cholangiocarcinoma Cells. Cell Physiol Biochem. 2017;42(3):1073-1086. doi: 10.1159/000478758. Epub 2017 Jun 29. PubMed PMID: 28662515.

6: Kim HJ, Hwang KE, Park DS, Oh SH, Jun HY, Yoon KH, Jeong ET, Kim HR, Kim YS. Shikonin-induced necroptosis is enhanced by the inhibition of autophagy in non-small cell lung cancer cells. J Transl Med. 2017 May 31;15(1):123. doi: 10.1186/s12967-017-1223-7. PubMed PMID: 28569199; PubMed Central PMCID: PMC5452303.

7: Wang TY, Zhou QL, Li M, Shang YX. Shikonin alleviates allergic airway remodeling by inhibiting the ERK-NF-κB signaling pathway. Int Immunopharmacol. 2017 Jul;48:169-179. doi: 10.1016/j.intimp.2017.05.011. Epub 2017 May 15. PubMed PMID: 28521243.

8: Li X, Fan XX, Jiang ZB, Loo WT, Yao XJ, Leung EL, Chow LW, Liu L. Shikonin inhibits gefitinib-resistant non-small cell lung cancer by inhibiting TrxR and activating the EGFR proteasomal degradation pathway. Pharmacol Res. 2017 Jan;115:45-55. doi: 10.1016/j.phrs.2016.11.011. Epub 2016 Nov 15. PubMed PMID: 27864022.

9: Jeung YJ, Kim HG, Ahn J, Lee HJ, Lee SB, Won M, Jung CR, Im JY, Kim BK, Park SK, Son MJ, Chung KS. Shikonin induces apoptosis of lung cancer cells via activation of FOXO3a/EGR1/SIRT1 signaling antagonized by p300. Biochim Biophys Acta. 2016 Nov;1863(11):2584-2593. doi: 10.1016/j.bbamcr.2016.07.005. Epub 2016 Jul 21. PubMed PMID: 27452907.

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