1946-74-3

Basic information

• Product Name: ?-THUJAPLICIN
• Synonyms: ?-THUJAPLICIN;2-Hydroxy-3-isopropyl-2,4,6-cycloheptatriene-1-one;2-Hydroxy-3-isopropylcyclohepta-2,4,6-trien-1-one
• CAS NO: 1946-74-3
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20
• Mol File: 1946-74-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 34 °C
• Boiling Point: 302.8°C at 760 mmHg
• Flash Point: 127.9°C
• Appearance: /
• Density: 1.127g/cm³
• Vapor Pressure: 9.33E-05mmHg at 25°C
• Refractive Index: 1.553
• PKA: 7.40±0.40(Predicted)
• CAS DataBase Reference: ?-THUJAPLICIN(CAS DataBase Reference)
• NIST Chemistry Reference: ?-THUJAPLICIN(1946-74-3)
• EPA Substance Registry System: ?-THUJAPLICIN(1946-74-3)

Safety Data

• Hazardous Substances Data: 1946-74-3(Hazardous Substances Data)

Usage

Chemical Properties

A minor component of Thujopsis dolabrata Sieb. et Zucc. var. hondai Makino.

Hazard

A poison.

InChI:InChI=1/C10H12O2/c1-7(2)8-5-3-4-6-9(11)10(8)12/h3-7H,1-2H3,(H,11,12)

Upstream product

• 48124-36-3 3-isopropenyl tropolone 
• 20036-72-0 2-isopropylcycloheptanone 
• 62412-12-8 2-(benzyloxy)-7-bromocyclohepta-2,4,6-trien-1-one 
• 77367-70-5 2-benzyloxycyclohepta-2,4,6-trienone 
• 533-75-5 2-hydroxy-2,4,6-cycloheptatrien-1-one 
• 108-94-1 cyclohexanone 
• 855393-80-5 3-ethoxy-3-isopropyl-cycloheptane-1,2-dione 
• 855393-78-1 3-isopropyl-cycloheptane-1,2-dione 
• 66365-99-9 2-Isopropylcyclohepta-2,6-dienon 
• 66365-97-7 2-isopropyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 
• 33000-38-3 2-isopropyltropone 
• 1578-06-9 1,1,3-tribromo-4-methylpentan-2-one 

Downstream Products

• 92879-00-0 3-benzhydryl-6-isopropyltropolone 
• 92832-10-5 3-(α-ethoxy-4-methylbenzyl)-6-isopropyltropolone 
• 92832-11-6 3-(α-ethoxy-4-methoxybenzyl)-6-isopropyltropolone 
• 79-31-2 isobutyric Acid 

Relevant articles and documents

Biological activity of α-Thujaplicin, the minor component of Thujopsis dolabrata SIEB. et ZUCC. var. hondai MAKINO

α-Thujaplicin, a minor component of Thujopsis dolabrata Sieb. et Zucc. var. hondai Makino, which was synthesized, showed the antibacterial activity, phytogrowth-inhibitory effect, inhibition of carboxypeptidase A and cytotoxic effect. Antibacterial activity of α-thujaplicin on Enterococcus faecalis IFO-12965 [minimum inhibitory concentration (MIC): 1.56 μg/ml] was higher than that of gentamicin (MIC: 6.25 μg/ml) used as a positive control. Inhibitory activity of α-thujaplicin on carboxypeptidase A [50% inhibitory concentration (IC50): 3.24×10-5 M] was higher than that of 1,10-phenanthroline used as a positive control. α-Thujaplicin showed germination inhibition toward the seed of Echinochloa utilis Ohwi et Yabuno even at the low concentration of 10 ppm and its growth inhibitory effect was stronger than that of sodium 2,4-dichlorophenoxyacetate used as a standard. α-Thujaplicin at 1.25 μg/ml inhibited cell growth of human stomach cancer KATO-III by 86%, and Ehrlich's ascites carcinoma by 87%, respectively. This compound even at the low concentration of 0.32 μg/ml also inhibited cell growth of the former by 66%, and the latter by 75%, respectively. The acute toxicity of α-thujaplicin [50% lethal dose (LD50) value: 256 mg/kg] in mice was as strong as those of β-dolabrin (LD50 value: 232 mg/kg) and γ-thujaplicin (LD50 value: 277 mg/kg).

Process for producing hinokitiol

A process for producing hinokitiol which comprises the step of obtaining 1-isopropylcyclopentadiene from cyclopentadiene and an isopropylating agent represented by the general formula R—X wherein R is an isopropyl group and X is a halogen or the like (first step), reacting it with a dihaloketene to obtain a ketene adduct (second step), and decomposing the ketene adduct (third step), said first step comprising the following three steps: a) a preparation step of cyclopentadienyl metal; b) a step of obtaining isopropylcyclopentadiene by isopropylating the cyclopentadienyl metal in an aprotic polar solvent; and c) a step of isomerizing 5-isopropylcyclopentadiene in the product selectively to 1-isopropylcyclopentadiene with heat.

NATURAL PRODUCT SYNTHESIS VIA THE POLYBROMO KETONE-IRON CARBONYL REACTION

Application of the polybromo ketone-iron carbonyl reaction to natural product synthesis is summarized.The general synthesis of tropane alkaloids has been achieved via the reductive cyclocoupling of sym-tetrabromoacetone with N-methoxycarbonylpyrrole as the key step.Ready availability of 8-oxabicyclooct-6-en-3-one from the tetrabromoacetone and furan has opened a new, efficient entry to natural C-nucleosides including pseudouridine, pseudocytidine, and showdomycin.The artificial analogues such as 2-thiopseudouridine, 6-azapseudouridine, pseudoisocytidine, etc., are also obtainable.The oxabicyclic ketones bearing an isopropyl substituent at the appropriate position serve as intermediates for the synthesis of naturally occurring troponoids, nezukone, α-thujaplicin, and hinokitiol (β-thujaplicin).Carbocamphenilone and camphenic acid have been prepared through the reaction of 1,1,3-tribromo-3-methylbutan-2-one and cyclopentadiene.The cyclocondensation of α,α'-dibromo ketone and a styrene derivative leads to the single-step synthesis of α-cuparenone. 1,3-Dibromo-3,7-dimethyloct-6-en-2-one derived from nerol (or geraniol) undergoes the biogenetic-type double cyclization.The iron carbonyl-assisted intramolecular cyclocoupling gives camphor accompanied by other monoterpenic ketones.A mixture of campherenone and epicampherenone has been obtained from related dibromo ketone prepared from farnesols.The hetero reaction by use of dibromo ketones and N,N-dimethylcarboxamides, forming 3 (2H)-furanones, is employable for the preparation of muscarine alkaloid derivatives.