517-89-5 Usage
Description
5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione is a naphthoquinone derivative with angiogenesis inhibitor properties. It is a naturally occurring compound that can be found in certain plants and is used for various applications due to its unique chemical structure and biological activities.
Uses
Used in Pharmaceutical Industry:
5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione is used as an angiogenesis inhibitor for its potential role in the development of new drugs targeting cancer and other diseases that rely on the formation of new blood vessels for growth and progression.
Used in Cosmetic Industry:
5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione is used as an ingredient in the cosmetic industry, likely due to its potential benefits for skin health and its ability to inhibit angiogenesis, which may help reduce the appearance of redness and inflammation.
Used in Traditional Chinese Medicine:
5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione, as a component of the plant Lithospermum erythrorhizon, is used in traditional Chinese medicine for the treatment of inflammatory diseases such as macular eruptions, measles, sore throat, carbuncles, and burns.
Used in Dye Industry:
As a derivative of shikonin, which is known to produce violet to gray colors on fabrics, 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione may be used as a mordant dye in the textile industry, particularly for creating vibrant and long-lasting colors.
Physical properties:
5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione appears as purple lamellae or crystalline powder with a melting point of 147 °C. It has a specific optical rotation of +138° (in benzene) and is soluble in ethanol, vegetable oils, and other organic solvents.
History
Kuroda and Majima firstly identified acetyl shikonin from L. erythrorhizon in 1922
, followed by the discovery of other shikonin derivatives, including shikonin. The
chemical structure of shikonin was not precisely identified till 1936 for its high
physicochemical similarity with naphthazarin . There have been about 500 publications
on shikonin up to now. Great attention has also been paid on the biosynthesis
of shikonin and its derivatives, and an increasing number of shikonin derivatives
have been designed and synthesized for exploring their antitumor effect. There are
two types of derivatives: one is modifications of 1′-OH with parent nucleus naphthazarin
remained and the other is modifications of both
1′-OH and parent nucleus naphthazarin, as shown in Fig. 3c, d .
Pharmacology
Shikonin possesses anti-inflammatory, antioxidant, antiviral, cardiovascular protective,and antitumor activities. Shikonin reduces inflammation by inhibiting the biosynthesis of leukotrienes and 5-hydroxyeicosatetraenoic acid and thus reduces synthesis of inflammation-related active molecules, which selectively block chemokine binding to CC chemokine receptor 1 . Shikonin shows free radical scavenging and antioxidant (especially toward superoxide anion and DPPH) activities. It significantly inhibits autoxidation caused by β-carotene and linoleic acid . Its anti-HCV effects have been reported recently with an EC50 at 25 ng/mL, which is lower than that of ribavirin (2.6 μg/mL) . Recent studies also reveal shikonin possesses cardiovascular protective effects. Shikonin inhibits the activity of TNF-α promoter, revealing its transcriptional antagonism to pro-inflammatory cytokine . Shikonin also shows antitumor potentials by inducing apoptosis and/or necrosis, inhibiting DNA topoisomerase activity and angiogenesis, and regulating proliferative signaling pathways (including MAPK, VEGF, and PTKs ). In addition, shikonin circumvents cancer drug resistance by induction of necroptotic cell death .
Clinical Use
Shikonin and its derivatives have not been approved for clinical use yet. Studies are
confined to cellular and animal experiments. Its original plant Zicao has a long history
of medical use both orally and externally in China. Various dosage forms of
Zicao, including tablets, injections, oils, creams, tinctures, plastics, and pastes, have
been developed for different clinical applications especially in dermatology, gynecology,
pediatrics, ophthalmology, and otorhinolaryngology. Among them, puccoon
oil and lithospermum cream are the most widely used forms.
Check Digit Verification of cas no
The CAS Registry Mumber 517-89-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 7 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 517-89:
(5*5)+(4*1)+(3*7)+(2*8)+(1*9)=75
75 % 10 = 5
So 517-89-5 is a valid CAS Registry Number.
InChI:InChI=1/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/t10-/m1/s1
517-89-5Relevant articles and documents
A novel and efficient total synthesis of shikonin
Wang, Rubing,Guo, Hui,Cui, Jiahua,Li, Shaoshun
, p. 3977 - 3980 (2012)
A novel and efficient synthesis of shikonin was accomplished with excellent enantiomeric excess (99.3% ee) and high overall yield (47%) in only six steps. The synthetic strategy involved an efficient Ru(II)-catalyzed asymmetric hydrogenation employing C2-symmetric planar chiral ruthenocene phosphinooxazoline ligand (L-3), followed by the subsequent removal of the methyl protecting groups. Meanwhile, it could be preliminarily confirmed that the chiral side chain of shikonin was difficult to be constructed in one step with both stereoselectivity and α-regioselectivity.
An improved and practical synthesis route to antiproliferative (±)-shikonin and its O-acyl derivatives
Ono, Mana,Abe, Shouki,Higai, Koji,Higashi, Shoko,Saito, Setsuo,Saito, Ryota
, p. 738 - 746 (2020/12/09)
Shikonin and its O-acyl derivatives are attracting increasing levels of attention among medicinal chemists due to their potencies as highly selective cytotoxic agents against cancer cells. However, providing a large number of shikonin-related samples by organic synthesis remains challenging. In the present study, we developed an improved and practical synthesis route to shikonin derivatives by olefin metathesis that has enabled the gram-scale preparation of a prenylated tetramethylnaphthazaline, a key intermediate in the synthesis of shikonin. In addition, a method for the selective cleavage of the acyl protecting groups at the phenolic positions of tri-O-acylated shikonins has been developed that provides concise routes to diverse O-acylshikonin derivatives.
Tigloylshikonin, a new minor shikonin derivative, from the roots and the commercial root extract of Lithospermum erythrorhizon
Ito, Yusai,Onobori, Kenichi,Yamazaki, Takeshi,Kawamura, Yoko
experimental part, p. 117 - 119 (2011/02/28)
Tigloylshikonin, a new shikonin derivative esterified with tiglic acid ((E)-2-methylbut-2-enoic acid), was isolated as a minor pigment from a food colorant "Shikon color," a commercial root extract from Lithospermum erythrorhizon SIEBOLD et ZUCCARINI. The structure of tigloylshikonin was elucidated using 1H, 13C, the difference nuclear Overhauser effect (NOE), and 2D NMR techniques. Its stereochemistry was determined by chiral-phase HPLC analysis. Tigloylshikonin was also found in the roots of L. erythrorhizon, which indicated that this new shikonin derivative is a typical component of naphthoquinone pigments in the roots of L. erythrorhizon.