Shikonin - ≥98%(HPLC) , CAS No.54952-43-1

CAS: 54952-43-1 Cat. No.: S170939 Molecular Weight: 288.3 EC Number: 684-467-1 PubChem CID: 5208

GRADE & PURITY ≥98%(HPLC)

Synonyms

HY-N6004 | LS-14485 | SCHEMBL14305203 | QTL1_000075 | 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (S)- | 3-(2,2-Dimethylpropionylamino)isonicotinicacid | BDBM178090 | KBio3_001080 | KBioGR_000610 | shikonin | 1, 5,8-dihydroxy-6-(1-hydroxy-4-methy

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

(±)-Shikonin is a racemic mixture of naturally occuring isohexenylnaphthazarin compounds which may contribute to antibacterial and anti-inflammatory activity.

Specifications

Synonyms

HY-N6004 | LS-14485 | SCHEMBL14305203 | QTL1_000075 | 1, 5, 8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (S)- | 3-(2, 2-Dimethylpropionylamino)isonicotinicacid | BDBM178090 | KBio3_001080 | KBioGR_000610 | shikonin | 1, 5, 8-dihydroxy-6-(1-hydroxy-4-methy

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Shikonin is a potent anti-fungal agent against C. albicans biofilms. It displays anti-oxidant and chemotherapeutic properties on human glioma cells. Naphthoquinone isolated from Arnebia sp. Used as an anti-inflammatory treatment in traditional chinese med

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%(HPLC)

Names and Identifiers

• Canonical Smiles: CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
• IUPAC Name: 5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
• InChIKey: NEZONWMXZKDMKF-UHFFFAOYSA-N
• INCHI: 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
• Isomeric SMILES: CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
• PubChem CID: 5208
• Molecular Weight: 288.3

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes
      • Subclass Naphthoquinones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Naphthoquinones
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthoquinones
• Alternative Parents: Bicyclic monoterpenoids Aromatic monoterpenoids Quinones Aryl ketones 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Secondary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthoquinone - Aromatic monoterpenoid - Bicyclic monoterpenoid - Monoterpenoid - Aryl ketone - Quinone - 1-hydroxy-2-unsubstituted benzenoid - Vinylogous acid - Ketone - Secondary alcohol - Hydrocarbon derivative - Alcohol - Organic oxide - Organic oxygen compound - Organooxygen compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
• External Descriptors: a secondary metabolite - a quinone

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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A498 (42825 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: methanol: 1 mg/mL
• Sensitivity: Heat & Moisture sensitive
• Molecular Weight: 288.290 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 288.1 Da
• Monoisotopic Mass: 288.1 Da
• Topological Polar Surface Area: 94.800 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 501.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Chen Xiaohui, Lin Shengrong, Liang Yunbang, Xue Xiaomin, Yasen Miersalijiang.  (2023)  Experimental evidence of shikonin as a novel intervention for anti-inflammatory effects.  NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY,      [PMID:37249613] [10.1007/s00210-023-02542-1]

2. Wenjie Feng, Wanrui Shi, Ze Wang, Yanqi Cui, Xinxin Shao, Shuwei Liu, Li Rong, Yi Liu, Hao Zhang.  (2022)  Enhancing Tumor Therapy of Fe(III)-Shikonin Supramolecular Nanomedicine via Triple Ferroptosis Amplification.  ACS Applied Materials & Interfaces,      [PMID:35944147] [10.1021/acsami.2c11130]

3. Yang Chen, Leting Si, Jinghui Zhang, Hengyuan Yu, Xuesong Liu, Yong Chen, Yongjiang Wu.  (2021)  Uncovering the antitumor effects and mechanisms of Shikonin against colon cancer on comprehensive analysis.  PHYTOMEDICINE,      [PMID:33476976] [10.1016/j.phymed.2021.153460]

4. Yang Chen, Juan Ni, Yun Gao, Jinghui Zhang, Xuesong Liu, Yong Chen, Zhongjian Chen, Yongjiang Wu.  (2020)  Integrated proteomics and metabolomics reveals the comprehensive characterization of antitumor mechanism underlying Shikonin on colon cancer patient-derived xenograft model..  Scientific Reports,  10  (1): (14092-14092).  [PMID:32839531] [10.1038/s41598-020-71116-5]

5. Hongli Guo, Jieyu Sun, Deyi Li, Yahui Hu, Xiaowen Yu, Hu Hua, Xia Jing, Feng Chen, Zhanjun Jia, Jing Xu.  (2019)  Shikonin attenuates acetaminophen-induced acute liver injury via inhibition of oxidative stress and inflammation.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:30818140] [10.1016/j.biopha.2019.108704]

6. Yali Zhang, Tingting Xu, Zheer Pan, Xiangting Ge, Chuchu Sun, Chun Lu, Hongjin Chen, Zhongxiang Xiao, Bing Zhang, Yuanrong Dai, Guang Liang.  (2017)  Shikonin inhibits myeloid differentiation protein 2 to prevent LPS-induced acute lung injury.  BRITISH JOURNAL OF PHARMACOLOGY,  175  (5): (840-854).  [PMID:29243243] [10.1111/bph.14129]

7. Wang Rong, Zhu Liangqin, Wang Jianfei, Zeng Chenglong, Chen Ying, Wei Yan.  (2025)  Electrochemical sensing interface of copper-coordinated polyhistidine/functionalized multi-walled carbon nanotubes for shikonin determination.  JOURNAL OF SOLID STATE ELECTROCHEMISTRY,      [PMID:] [10.1007/s10008-025-06244-x]

8. Zhiyuan Liu, Yaxuan Huang, Rui Sun, Nan Li, Fengyun Xu, Wei Zhang, Wenke Zhang.  (2025)  Polyethylene Glycolated Shikonin-Functionalized Carbon Nanotubes as an Effective Anticancer System Combining Chemotherapy and Photothermal Therapy.  LANGMUIR,      [PMID:40015981] [10.1021/acs.langmuir.4c05257]

9. Wenjie Feng, Wanrui Shi, Shuwei Liu, Huiwen Liu, Yi Liu, Pengfei Ge, Hao Zhang.  (2021)  Fe(III)-Shikonin Supramolecular Nanomedicine for Combined Therapy of Tumor via Ferroptosis and Necroptosis.  Advanced Healthcare Materials,  11  (2): (2101926).  [PMID:34738742] [10.1002/adhm.202101926]