86630-46-8

Basic information

• Product Name: Nudol
• Synonyms: Nudol;3,4-Dimethoxy-2,7-phenanthrenediol
• CAS NO: 86630-46-8
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.27996
• Mol File: 86630-46-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 512.4°Cat760mmHg
• Flash Point: 263.7°C
• Appearance: /
• Density: 1.334g/cm³
• Vapor Pressure: 4.04E-11mmHg at 25°C
• Refractive Index: 1.709
• CAS DataBase Reference: Nudol(CAS DataBase Reference)
• NIST Chemistry Reference: Nudol(86630-46-8)
• EPA Substance Registry System: Nudol(86630-46-8)

Safety Data

• Hazardous Substances Data: 86630-46-8(Hazardous Substances Data)

Usage

Description

Nudol is a chemical compound belonging to the pyrophosphate family, specifically functioning as a Ca2+-dependent pyrophosphatase inhibitor. It is recognized for its capacity to inhibit the enzyme site of phosphate transfer and impede the hydrolysis of ATP to AMP and pyrophosphate. This inhibition leads to the accumulation of both substrates and end products, potentially disrupting cellular metabolism. Nudol plays a significant role in the study of cellular processes and holds promise for applications in pharmaceutical and biochemical research.

Uses

Used in Pharmaceutical Research:
Nudol is used as a research tool for understanding the role of pyrophosphatase enzymes in cellular metabolism and their potential as therapeutic targets. Its ability to inhibit these enzymes can provide insights into the development of new drugs targeting metabolic pathways.
Used in Biochemical Research:
In the field of biochemical research, Nudol is utilized as an inhibitor to study the effects of disrupted ATP hydrolysis on cellular processes. This can aid in the exploration of alternative energy sources and metabolic pathways within cells.
Used in Drug Development:
Nudol is employed as a lead compound in the development of new pharmaceuticals that target pyrophosphatase enzymes. Its inhibitory properties can be harnessed to create drugs that modulate cellular metabolism for the treatment of various diseases.
Used in Cellular Metabolism Studies:
In cellular metabolism studies, Nudol is used as an experimental agent to investigate the consequences of inhibiting key enzymes involved in energy production and transfer. This can contribute to a better understanding of cellular energy dynamics and the potential for metabolic intervention.

InChI:InChI=1/C16H14O4/c1-19-15-13(18)8-10-4-3-9-7-11(17)5-6-12(9)14(10)16(15)20-2/h3-8,17-18H,1-2H3

Synthetic route

2,3,4,7-tetramethoxyphenanthrene (97399-69-4) → 2,7-dihydroxy-3,4-dimethoxyphenanthrene (86630-46-8)

Conditions	Yield
With aluminium trichloride; ethanethiol In dichloromethane at -10℃; for 0.5h;	60%

2,7-diacetoxy-3,4-dimethoxyphenanthrene (86630-45-7) → 2,7-dihydroxy-3,4-dimethoxyphenanthrene (86630-46-8)

Conditions	Yield
With potassium hydroxide In methanol for 3h; Heating;

acetic anhydride (108-24-7) + 2,7-dihydroxy-3,4-dimethoxyphenanthrene (86630-46-8) → 2,7-diacetoxy-3,4-dimethoxyphenanthrene (86630-45-7)

Conditions	Yield
With pyridine In dichloromethane at 20 - 25℃;	82.44%
With pyridine Ambient temperature;

2,7-dihydroxy-3,4-dimethoxyphenanthrene (86630-46-8) → 2,2',7,7'-tetrahydroxy-3,3',4,4'-tetramethoxy-1,1'-biphenanthryl (138730-52-6)

Conditions	Yield
With phosphomolybdic acid; silica gel In Petroleum ether for 6h;	80%
With silica gel impregnated with phosphomolybdic acid In petrol for 6h;	80%
With air In dichloromethane at 0℃; for 20h;	76%

2,7-dihydroxy-3,4-dimethoxyphenanthrene (86630-46-8) + methyl iodide (74-88-4) → 2,3,4,7-tetramethoxyphenanthrene (97399-69-4)

Conditions	Yield
With potassium carbonate In acetone at 20 - 25℃;	79.19%

2,7-dihydroxy-3,4-dimethoxyphenanthrene (86630-46-8) → (-)-2,2',7,7'-tetrahydroxy-3,3',4,4'-tetramethoxy-1,1'-biphenanthryl

Conditions	Yield
With CuCl(OH)*(-)-(S)-proline methyl ester reagent; oxygen In methanol; dichloromethane for 25h; Cooling with ice; optical yield given as %ee;	75%

3,4-diacetoxycinnamoyl chloride (98631-72-2, 82592-68-5) + 2,7-dihydroxy-3,4-dimethoxyphenanthrene (86630-46-8) → 3,4-dimethoxyphenanthrene-2,7-bis-[(2E)-3-[3,4-bis(acetyloxy)phenyl]acrylate] (1144103-62-7)

Conditions	Yield
In dichloromethane at 20 - 25℃;	47%

Upstream product

• 97399-69-4 2,3,4,7-tetromethoxyphenanthrene 
• 86630-45-7 2,7-diacetoxy-3,4-dimethoxyphenanthrene 

Downstream Products

• 1144103-62-7 3,4-dimethoxyphenanthrene-2,7-bis-[(2E)-3-[3,4-bis(acetyloxy)phenyl]acrylate] 

Relevant articles and documents

NUDOL, A PHENANTHRENE OF THE ORCHIDS EULOPHIA NUDA, ERIA CARINATA AND ERIA STRICTA

Euolophia nuda; Eria carinata; Eria stricta; Orchidaceae; 2,7-dihydroxy-3,4-dimethoxyphenanthrene.An amorphous phenanthrene, named nudol has been isolated from Eulophia nuda, Eria carinata and E. stricta.It was identified as 2,7-dihydroxy-3,4-dimethoxyphenanthrene.Synthesis of nudol and its dimethyl ether is described.