16274-34-3

Basic information

• Product Name: 1-Hydroxy-2-prenylnaphthalene
• Synonyms: 1-Hydroxy-2-prenylnaphthalene;2-(3-Methyl-2-butenyl)-1-naphthol;2-Prenyl-1-naphthol;2-(3-Methylbut-2-en-1-yl)naphthalen-1-ol
• CAS NO: 16274-34-3
• Molecular Formula: C₁₅H₁₆O
• Molecular Weight: 212
• Mol File: 16274-34-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 358.1±11.0 °C(Predicted)
• Appearance: /
• Density: 1.073±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 9.88±0.50(Predicted)
• CAS DataBase Reference: 1-Hydroxy-2-prenylnaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy-2-prenylnaphthalene(16274-34-3)
• EPA Substance Registry System: 1-Hydroxy-2-prenylnaphthalene(16274-34-3)

Safety Data

• Hazardous Substances Data: 16274-34-3(Hazardous Substances Data)

Usage

General Description

1-Hydroxy-2-prenylnaphthalene, also known as plumbagin, is a naturally occurring chemical compound found in plants such as the Plumbago genus. It is a yellow pigment that has been used historically as a dye and in traditional medicine for its antibacterial, antifungal, and antiprotozoal properties. Plumbagin has also shown potential as an anticancer agent, with research indicating its ability to inhibit the growth of various cancer cells. Additionally, it has demonstrated anti-inflammatory and antioxidant properties, making it a subject of interest in the development of new pharmaceuticals. However, the use of plumbagin is still limited due to its potential toxicity and further research is needed to fully understand its pharmacological effects.

Upstream product

• 574-00-5 1,2-Dihydroxynaphthalene 
• 870-63-3 prenyl bromide 
• 598-25-4 Dimethylallene 
• 90-15-3 α-naphthol 
• 115-18-4 2-methyl-3-buten-2-ol 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 78-79-5 isoprene 
• 20213-31-4 1-naphthyl prenyl ether 
• 87-41-2 2-benzofuran-1(3H)-one 
• 54109-51-2 ethyl 5-methyl-2-methylenehex-4-enoate 

Downstream Products

• 16274-33-2 3,4-dihydro-2,2-dimethyl-2H-naphtho[1,2-b]-pyran 

Relevant articles and documents

Benzannulation for the regiodefined synthesis of 2-alkyl/aryl-1-naphthols: Total synthesis of arnottin i

The annulation of phthalides with α-alkyl/arylacrylates in the presence of LDA/LHMDS is shown to directly give alkyl/aryl-1-naphthols. The method involving a novel dealkoxycarbonylation obviates the regiochemical issues in the synthesis of polysubstituted naphthalenes, and it forms the key step in a three-step total synthesis of arnottin I, a naphthobenzopyranone natural product.

Bismuth triflate catalyzed [1,3] rearrangement of aryl 3-methylbut-2-enyl ethers

An efficient bismuth triflate catalyzed [1,3] rearrangement of aryl 3-methylbut-2-enyl ethers has been developed. The reaction proceeds rapidly and affords the corresponding para- and ortho-prenylated phenols and naphthols in moderate to good yields (up t

Water-Accelerated Claisen Rearrangements

Allyl aryl ethers undergo accelerated Claisen and [1,3] rearrangements in the presence of a mixture of trialkylalanes and water or aluminoxanes. The ratio of ortho-, meta-, and pora-Claisen products depends to a large extent on the presence of water and to a much lesser extent on the nature of the alane.