Hinokitiol supplier | CasNO.499-44-5

Name
Hinokitiol
EINECS 207-880-7
CAS No. 499-44-5
Article Data24
CAS DataBase
Density 1.127 g/cm³
Solubility insoluble in water
Melting Point 50-52 °C
Formula C₁₀H₁₂O₂
Boiling Point 303.4 °C at 760 mmHg
Molecular Weight 164.204
Flash Point 128.1 °C
Transport Information
Appearance
Safety 36
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 2,4,6-Cycloheptatrien-1-one,2-hydroxy-4-isopropyl- (6CI,8CI);2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one;4-Isopropyltropolone;6-Isopropyltropolone;HT-SF;Hinokitiol;Hyka 1;IPT;Kisei Pro-Sol N;NSC 18804;S-HT;b-Isopropyltropolon;b-Thujaplicin;b-Thujaplicine;
PSA 37.30000
LogP 1.87580

Synthetic route

: 55076-49-8
2-amino-6-isopropyl-cycloheptatrienone

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
With potassium hydroxide	100%

: 4570-11-0
β-dolabrin

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 22℃; under 760 Torr; for 6.5h;	98%
With hydrogen; palladium on activated charcoal In ethanol	98%

: 52732-22-6
isopropanol boric acid

: 698-48-6
2-hydroxy-4-chloro-2,4,6-cycloheptatrien-1-one

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
With potassium phosphate In tetrahydrofuran at 100℃; for 2h;	97.5%

: 310905-95-4
(5S)-6-isopropyl-3-cycloheptene-1,2-dione

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
Stage #1: (5S)-6-isopropyl-3-cycloheptene-1,2-dione With pyrrolidone hydrotribromide In tetrahydrofuran at 20℃; for 1h; Bromination; Stage #2: With lithium carbonate; lithium bromide In N,N-dimethyl-formamide for 2h; Aromatisation; Heating;	71%

: 698-47-5
4-bromo-2-hydroxycycklohepta-2,4,6-trien-1-one

: 3043-46-7
isopropenyltrimethylstannane

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
Stage #1: 4-bromo-2-hydroxycycklohepta-2,4,6-trien-1-one; isopropenyltrimethylstannane With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane for 1h; Reflux; Stage #2: With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr; for 24h;	53%

: 13656-84-3
4-isopropyl-cycloheptanone

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
With selenium(IV) oxide; ethanol Erwaermen des Reaktionsprodukts mit N-Brom-succinimid in CHCl3;

: 13656-84-3
4-isopropyl-cycloheptanone

A: 499-44-5
hinokitiol

B: 2891-67-0
3-bromo-5-isopropyl-tropolone

Conditions

Conditions	Yield
With selenium(IV) oxide; ethanol Behandeln des Reaktionsprodukts mit Brom in Essigsaeure und Erhitzen des hierbei erhaltenen Reaktionsprodukts mit Wasserdampf;

: 108168-72-5
3-isopropylcycloheptanone

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
With selenium(IV) oxide; ethanol Erwaermen des Reaktionsprodukts mit N-Brom-succinimid in CHCl3;
Multi-step reaction with 2 steps 1: selenium dioxide / ethanol; H2O / 2 h / 90 °C 2: 1.) phenyltrimethylammonium tribromide 2.) LiCl, Li2CO3 / 1.) THF, RT, 1.75 h, 2.) DMF, 120 deg C, 45 min View Scheme

: (1S,5R)-7,7-Dichloro-1-isopropyl-bicyclo[3.2.0]hept-2-en-6-one

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
With potassium acetate

: (1R,5S)-7,7-Dichloro-3-isopropyl-bicyclo[3.2.0]hept-2-en-6-one

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
With potassium acetate

: 499-44-5
2-hydroxy-6-isopropyl-2,4,6-cycloheptatrien-1-one

A: 931-88-4, 931-87-3
(Z)-Cyclooctene

B: 499-44-5
hinokitiol

Conditions

Conditions	Yield
In decalin at 180℃; for 4h;	A 95 % Spectr. B n/a

: 499-44-5
2-hydroxy-6-isopropyl-2,4,6-cycloheptatrien-1-one

A: 499-44-5
hinokitiol

B: 142-29-0
cyclopentene

Conditions

Conditions	Yield
In decalin at 180℃; for 3h;	A n/a B 95 % Spectr.

: 108168-73-6
4-isopropylcycloheptane-1,2-dione

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
With C6H5N(1+); lithium chloride Yield given. Multistep reaction;
With phenyltrimethylammonium tribromide; lithium carbonate; lithium chloride 1.) THF, RT, 1.75 h, 2.) DMF, 120 deg C, 45 min; Yield given. Multistep reaction;

: 66967-15-5
2-chloro-6-isopropyl-cycloheptatrienone

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
With phosphoric acid; acetic acid

: 66967-10-0
2-chloro-5-isopropyltropone

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
With phosphoric acid; acetic acid Heating;

/PBWLC126-1000/: /PBWLC126-1000/

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
oxidation;

: 105897-85-6
(R)-3-(1-methylethyl)-6-oxoheptanal dimethylacetal

A: 499-44-5
hinokitiol

B 2-bromoprop-2-enyl halide: 2-bromoprop-2-enyl halide

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 1.2: tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: TiCl4 / CH2Cl2 / 0.17 h / -78 °C 3.1: 63 percent / p-TsOH; 4 Angstroem molecular sieves / benzene / 1 h / Heating 4.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 4.2: tetrahydrofuran; hexane / 0.5 h / -15 - 20 °C 5.1: MCPBA / hexane / 4 h / 20 °C 5.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 6.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 7.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C 7.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme

Yield

Multi-step reaction with 7 steps
1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C
1.2: tetrahydrofuran; hexane / 2 h / -78 - 20 °C
2.1: TiCl4 / CH2Cl2 / 0.17 h / -78 °C
3.1: 63 percent / p-TsOH; 4 Angstroem molecular sieves / benzene / 1 h / Heating
4.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C
4.2: tetrahydrofuran; hexane / 0.5 h / -15 - 20 °C
5.1: MCPBA / hexane / 4 h / 20 °C
5.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C
6.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
7.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C
7.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating
View Scheme

: 310905-92-1
(5R)-5-isopropyl-2-cyclohepten-1-one

A: 499-44-5
hinokitiol

B 2-bromoprop-2-enyl halide: 2-bromoprop-2-enyl halide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 1.2: tetrahydrofuran; hexane / 0.5 h / -15 - 20 °C 2.1: MCPBA / hexane / 4 h / 20 °C 2.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 3.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 4.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C 4.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme

Yield

Multi-step reaction with 4 steps
1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C
1.2: tetrahydrofuran; hexane / 0.5 h / -15 - 20 °C
2.1: MCPBA / hexane / 4 h / 20 °C
2.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C
3.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
4.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C
4.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating
View Scheme

: 310905-94-3
(5S)-7-hydroxy-5-isopropyl-2-cyclohepten-1-one

A: 499-44-5
hinokitiol

B 2-bromoprop-2-enyl halide: 2-bromoprop-2-enyl halide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 2.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C 2.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme

: 310905-91-0
(5R)-5-isopropyl-3-methoxycycloheptanone

A: 499-44-5
hinokitiol

B 2-bromoprop-2-enyl halide: 2-bromoprop-2-enyl halide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 63 percent / p-TsOH; 4 Angstroem molecular sieves / benzene / 1 h / Heating 2.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 2.2: tetrahydrofuran; hexane / 0.5 h / -15 - 20 °C 3.1: MCPBA / hexane / 4 h / 20 °C 3.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 4.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 5.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C 5.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 63 percent / p-TsOH; 4 Angstroem molecular sieves / benzene / 1 h / Heating
2.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C
2.2: tetrahydrofuran; hexane / 0.5 h / -15 - 20 °C
3.1: MCPBA / hexane / 4 h / 20 °C
3.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C
4.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
5.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C
5.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating
View Scheme

: 310905-93-2
((S)-4-Isopropyl-cyclohepta-1,6-dienyloxy)-trimethyl-silane

A: 499-44-5
hinokitiol

B 2-bromoprop-2-enyl halide: 2-bromoprop-2-enyl halide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: MCPBA / hexane / 4 h / 20 °C 1.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 2.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 3.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C 3.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme

: 310905-90-9
[(R)-4-(2,2-Dimethoxy-ethyl)-5-methyl-1-methylene-hexyloxy]-trimethyl-silane

A: 499-44-5
hinokitiol

B 2-bromoprop-2-enyl halide: 2-bromoprop-2-enyl halide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: TiCl4 / CH2Cl2 / 0.17 h / -78 °C 2.1: 63 percent / p-TsOH; 4 Angstroem molecular sieves / benzene / 1 h / Heating 3.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 3.2: tetrahydrofuran; hexane / 0.5 h / -15 - 20 °C 4.1: MCPBA / hexane / 4 h / 20 °C 4.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 5.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 6.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C 6.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme

Yield

Multi-step reaction with 6 steps
1.1: TiCl4 / CH2Cl2 / 0.17 h / -78 °C
2.1: 63 percent / p-TsOH; 4 Angstroem molecular sieves / benzene / 1 h / Heating
3.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C
3.2: tetrahydrofuran; hexane / 0.5 h / -15 - 20 °C
4.1: MCPBA / hexane / 4 h / 20 °C
4.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C
5.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
6.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C
6.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating
View Scheme

: 698-47-5
4-bromo-2-hydroxycycklohepta-2,4,6-trien-1-one

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 54 percent / dichlorobis(triphenylphosphine)palladium(II) / dioxane / 1.3 h / Heating 2: 98 percent / hydrogen / 5percent Pd/C / ethanol View Scheme
Multi-step reaction with 2 steps 1: 54 percent / dichlorobis(triphenylphosphine)palladium(II) / dioxane / 1.33 h / Heating 2: 98 percent / H2 / 5percent Pd/C / ethanol / 6.5 h / 22 °C / 760 Torr View Scheme

: 1714-40-5
3-Methoxycyclohepta-1,3,5-triene

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Et4NOTs / dimethylformamide / electroreduction 2: 1.) pyridinium bromide perbromide 2.) LiCl/LiCO3 / 2.) DMF 3: 100 percent / NH2NH2 4: 100 percent / KOH View Scheme
Multi-step reaction with 5 steps 1: Et4NOTs / dimethylformamide / electroreduction 2: 87 percent / aq. H2SO4 / tetrahydrofuran 3: 82 percent / 30percent H2O2/NaOH 4: 72 percent / aq. HCl 5: 1.) C6H5N(1+) 2.) LiCl/LiCO3 View Scheme

: 1728-32-1
1-methoxycyclohepta-1,3,5-triene

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 2: 1.) pyridinium bromide perbromide 2.) LiCl/LiCO3 / 2.) DMF 3: 100 percent / NH2NH2 4: 100 percent / KOH View Scheme
Multi-step reaction with 5 steps 2: 87 percent / aq. H2SO4 / tetrahydrofuran 3: 82 percent / 30percent H2O2/NaOH 4: 72 percent / aq. HCl 5: 1.) C6H5N(1+) 2.) LiCl/LiCO3 View Scheme
Multi-step reaction with 4 steps 1: Et4NOTs / dimethylformamide / electroreduction 2: 1.) pyridinium bromide perbromide 2.) LiCl/LiCO3 / 2.) DMF 3: 100 percent / NH2NH2 4: 100 percent / KOH View Scheme
Multi-step reaction with 5 steps 1: Et4NOTs / dimethylformamide / electroreduction 2: 87 percent / aq. H2SO4 / tetrahydrofuran 3: 82 percent / 30percent H2O2/NaOH 4: 72 percent / aq. HCl 5: 1.) C6H5N(1+) 2.) LiCl/LiCO3 View Scheme

: 35193-01-2
β-isopropyltropolone

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / NH2NH2 2: 100 percent / KOH View Scheme

: 6-Isopropyl-cyclohept-3-enone

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 82 percent / 30percent H2O2/NaOH 2: 72 percent / aq. HCl 3: 1.) C6H5N(1+) 2.) LiCl/LiCO3 View Scheme

: 133826-10-5
1-methoxy-6-isopropyl-1,3-cycloheptadiene

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) pyridinium bromide perbromide 2.) LiCl/LiCO3 / 2.) DMF 2: 100 percent / NH2NH2 3: 100 percent / KOH View Scheme
Multi-step reaction with 4 steps 1: 87 percent / aq. H2SO4 / tetrahydrofuran 2: 82 percent / 30percent H2O2/NaOH 3: 72 percent / aq. HCl 4: 1.) C6H5N(1+) 2.) LiCl/LiCO3 View Scheme

: 4-Isopropyl-8-oxa-bicyclo[5.1.0]octan-2-one

: 499-44-5
hinokitiol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / aq. HCl 2: 1.) C6H5N(1+) 2.) LiCl/LiCO3 View Scheme

: 499-44-5
hinokitiol

: 32659-57-7
2-hydroxy-7-iodo-4-isopropyltropone

Conditions

Conditions	Yield
With sulfuric acid; iodine; potassium carbonate In chloroform	100%
With iodine; potassium carbonate In diethyl ether for 24h; Ambient temperature;	100%
With iodine	70%

: 110-85-0
piperazine

: 50-00-0
formaldehyd

: 499-44-5
hinokitiol

: 1211884-65-9
1,4-bis(6-hydroxy-4-isopropyl-7-oxo-1,3,5-cycloheptatrienylmethyl)piperazine

Conditions

Conditions	Yield
Stage #1: piperazine; formaldehyd; hinokitiol With acetic acid In methanol at 60℃; Mannich reaction; Stage #2: With sodium hydrogencarbonate In methanol; water	100%

...Expand

: 50-00-0
formaldehyd

: 120-43-4
4-ethoxycarbonylpiperazine

: 499-44-5
hinokitiol

: 1211884-44-4
4-(6-hydroxy-4-isopropyl-7-oxo-1,3,5-cycloheptatrienylmethyl)-1-piperazinecarboxylic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: formaldehyd; 4-ethoxycarbonylpiperazine; hinokitiol With acetic acid In methanol at 60℃; Mannich reaction; Stage #2: With sodium hydrogencarbonate In methanol; water	99%

...Expand

: 50-00-0
formaldehyd

: 499-44-5
hinokitiol

: 122003-27-4
(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)(piperazin-1-yl)methanone

: 1211884-55-7
1-[N-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-ylcarbonyl)]-4-(6-hydroxy-4-isopropyl-7-oxo-1,3,5-cycloheptatrienylmethyl)piperazine

Conditions

Conditions	Yield
Stage #1: formaldehyd; hinokitiol; (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)(piperazin-1-yl)methanone With acetic acid In methanol at 60℃; Mannich reaction; Stage #2: With sodium hydrogencarbonate In methanol; water	99%

...Expand

: 499-44-5
hinokitiol

: 74-88-4
methyl iodide

: 18448-52-7
4-isopropyltropolone methyl ether

Conditions

Conditions	Yield
With perhydrodibenzo-18-crown-6; potassium carbonate In acetonitrile for 10h; Heating;	96.4%

: 499-44-5
hinokitiol

: 109-63-7
trifluoroborane diethyl ether

: 2248-50-2
difluoro(3-isopropyl-7-oxo-1,3,5-cycloheptatrienyloxy)borane

Conditions

Conditions	Yield
In not given react. hinokitiol and boron trifluoride etherate; product recrystd. from chloroform-benzene (4:7);	96%

: 499-44-5
hinokitiol

: 98-59-9
p-toluenesulfonyl chloride

: 69141-46-4
4-(1-methylethyl)-2-[[(4-methylphenyl)sulfonyl]oxy]-2,4,6-cycloheptatrien-1-one

Conditions

Conditions	Yield
In pyridine	96%

: 499-44-5
hinokitiol

: OsHCl(CO)(P(p-tolyl)3)3

: C53H54O3OsP2

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene for 2.5h; Reflux; Inert atmosphere;	95%

: indium chloride

: 499-44-5
hinokitiol

: 154727-99-8, 16973-43-6
trans-{tris(4-iso-propyl-2-hydroxy-2,4,6-cycloheptatrien-1-onato-O,O')-indium(III)}

Conditions

Conditions	Yield
In ethanol refluxed; 1 h; left to stand for 48 h;; pptd. from H2O; crystd. after 48 h; washed with EtOH/H2O; dried over CaCl2; elem. anal.;;	91%

: 16971-31-6, 36007-23-5
hydridocarbonylchlorotris(triphenylphosphine)osmium(II)

: 499-44-5
hinokitiol

: C47H42O3OsP2

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene for 5.5h; Reflux; Inert atmosphere;	91%

: 110-91-8
morpholine

: 50-00-0
formaldehyd

: 499-44-5
hinokitiol

: 4-(4-isopropyl-6-hydroxy-7-oxo-1,3,5-cycloheptatrienylmethyl)morpholine

Conditions

Conditions	Yield
With acetic acid In methanol at 60℃; Mannich reaction;	88%

...Expand

: 157072-60-1, 61521-25-3, 166941-05-5, 16971-33-8
(carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II)

: 499-44-5
hinokitiol

: C47H42O3P2Ru

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene for 2.5h; Reflux; Inert atmosphere;	88%

: Iron(III) nitrate nonahydrate

: 499-44-5
hinokitiol

: 31396-80-2
tris(4-isopropyltropolonato)iron(III)

Conditions

Conditions	Yield
In methanol; ethanol to soln. of iron salt in MeOH was added to soln. of hinokitiol in MeOH, stirred for 1 h at room temp.; filtered, washed with EtOH, Et2O, dried in vac. for 2 h;	87.6%
In ethanol at 20℃; for 2h;	86.7%

: copper(ll) sulfate pentahydrate

: 499-44-5
hinokitiol

: 14076-63-2, 685836-60-6
[Cu(II)(4-isopropyltropolone)2] C20H22CuO4, monoclinic, P21/N

Conditions

Conditions	Yield
In ethanol; water to soln. of ligand in 1:1 mixt. EtOH and water (20 ml) was added CuSO4, soln. was refluxed for 2 h; soln. was passed through folded filter paper, filtrate was evapd. slowlyat room temp., after few days crystals were grown, ppt. collected, wash ed with H2O, dried in vac.; elem. anal.;	76.5%

: 499-44-5
hinokitiol

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: 3,4,5-trimethoxy-benzoic acid 3-isopropyl-7-oxo-cyclohepta-1,3,5-trienyl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane for 12h; Heating;	76%

: 499-44-5
hinokitiol

: 7550-45-0
titanium tetrachloride

: 1106674-51-4
[Ti(hinokitiol)2Cl2]

Conditions

Conditions	Yield
In methanol; diethyl ether to soln. of TiCl4 in ether was added soln. of hinokitiol in ether, stirred for 2 h at room temp.; filtered, washed with ether, dried in vac. for 2 h;	74.1%

: 2403-58-9
4-methoxybenzaldehyde diethylacetal

: 499-44-5
hinokitiol

: 92832-11-6
3-(α-ethoxy-4-methoxybenzyl)-6-isopropyltropolone

Conditions

Conditions	Yield
In toluene for 20h; Heating;	72%

: 313988-88-4
6-hydroxy-2,5,7,8-tetramethyl-N-(2-piperazinoethyl)-2-chromanecarboxamide

: 50-00-0
formaldehyd

: 499-44-5
hinokitiol

: 1211884-59-1
1-[N-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-ylcarbonyl)ethylamino]-4-(6-hydroxy-4-isopropyl-7-oxo-1,3,5-cycloheptatrienylmethyl)piperazine

Conditions

Conditions	Yield
Stage #1: 6-hydroxy-2,5,7,8-tetramethyl-N-(2-piperazinoethyl)-2-chromanecarboxamide; formaldehyd; hinokitiol With acetic acid In methanol at 60℃; Mannich reaction; Stage #2: With sodium hydrogencarbonate In methanol; water	71%

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: 15529-49-4, 41756-81-4
tris(triphenylphosphine)ruthenium(II) chloride

: 499-44-5
hinokitiol

: C56H52O4P2Ru

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol for 1.5h; Inert atmosphere; Reflux;	71%

: copper(ll) sulfate pentahydrate

: 499-44-5
hinokitiol

: [Cu(II)(4-isopropyltropolone)2]

Conditions

Conditions	Yield
In ethanol; water to soln. of ligand in 1:1 mixt. EtOH and water (30 ml) was added CuSO4, soln. was refluxed for 2 h; soln. was passed through folded filter paper, filtrate was evapd. slowlyat room temp., after few days crystals were grown, ppt. collected, wash ed with H2O, dried in vac.; elem. anal.;	70.7%

: 75802-22-1
1-ethoxyisochromane

: 499-44-5
hinokitiol

: 87864-22-0
3-(1-isochromanyl)-6-isopropyltropolone

Conditions

Conditions	Yield
at 150 - 160℃; for 6h;	66%
heating;

: 499-44-5
hinokitiol

: 100-07-2
4-methoxy-benzoyl chloride

: 4-methoxy-benzoic acid 3-isopropyl-7-oxo-cyclohepta-1,3,5-trienyl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane for 12h; Heating;	65%

: 499-44-5
hinokitiol

: 7789-61-9
antimony(III) bromide

: [Sb(III)(hinokitiol)2Br]

Conditions

Conditions	Yield
In methanol; benzene to soln. of SbBr3 in C6H6 was added soln. of hinokitiol in MeOH, stirredfor 2 h; filtered, evapd. in vac. at 30°C, dissolved in EtOH, filtered, filtrate slow evapd. at room temp., filtered, washed with cold EtOH, driedin vac. for 2 h;	62.5%

: 10025-69-1
tin(II) chloride dihdyrate

: 499-44-5
hinokitiol

: 58528-20-4
Sn(hinokitiol)2

Conditions

Conditions	Yield
In ethanol; water a soln. of hydroxyketone in ethanol was added a stirred soln. of Sn-compound in water under N2, the soln. was stirred for 1.5 h; filtered, ppt. was dried under vac.; elem. anal.;	56%

: 10602-34-3
1,1-diethoxy-but-2-ene

: 499-44-5
hinokitiol

: 92397-04-1
3-isopropyl-6-(1-ethoxy-2-butenyl)tropolone

Conditions

Conditions	Yield
at 160℃; for 5h;	55%

: 50-00-0
formaldehyd

: 499-44-5
hinokitiol

: 1-(3,4-dimethoxybenzoyl)piperazine

: 7-[4-(3-(3,4-dimethoxybenzoyl)piperazin-1-yl)methyl]-2-hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one

Conditions

Conditions	Yield
With acetic acid In methanol at 60℃;	55%

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Hinokitiol Consensus Reports

Reported in EPA TSCA Inventory.

Hinokitiol Specification

The IUPAC name of 4-Isopropyltropolone is 2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one. With the CAS registry number 499-44-5, it is also named as 2-Hydroxy-4-(1-methylethyl)-2,4,6-cycloheptatrien-1-one. The product's categories are Tropolones; Tropolones & Azulenes. It is a tropolone derivative and one of the thujaplicins. Additionally, this chemical should be sealed in the container and stored in the ventilate and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.89; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.88; (4)ACD/LogD (pH 7.4): 1.41; (5)ACD/BCF (pH 5.5): 15.72; (6)ACD/BCF (pH 7.4): 5.3; (7)ACD/KOC (pH 5.5): 248.21; (8)ACD/KOC (pH 7.4): 83.69; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.553; (13)Molar Refractivity: 46.67 cm³; (14)Molar Volume: 145.6 cm³; (15)Polarizability: 18.5×10^-24 cm³; (16)Surface Tension: 44.6 dyne/cm; (17)Enthalpy of Vaporization: 63.05 kJ/mol; (18)Vapour Pressure: 8.98E-05 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Tautomer Count: 34; (21)Exact Mass: 164.08373; (22)MonoIsotopic Mass: 164.08373; (23)Topological Polar Surface Area: 37.3; (24)Heavy Atom Count: 12; (25)Complexity: 280.

Preparation of 4-Isopropyltropolone: It is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. So it can be obtained by the wood of Chamaecyparis obtuse Sieb.et Zucc.

Uses of 4-Isopropyltropolone: It has inhibitory effects on Chlamydia trachomatis and may be clinically useful as a topical drug. And it also can react with 4-methoxy-benzaldehyde diethylacetal to get a,a-bis(2-hydroxy-6-isopropyltropon-3-yl)-4-methoxytoluene. This reaction may react at temperature of 180 °C. The reaction time is 2 hours. The yield is 34%.

When you are using this chemical, please be cautious about it as the following:
The 4-Isopropyltropolone is harmful if swallowed. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C1/C=C(\C=C/C=C1/O)C(C)C
2. InChI:InChI=1/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LDLo	subcutaneous	500mg/kg (500mg/kg)		Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 48, Pg. 722, 1959.
mouse	LD50	intraperitoneal	85mg/kg (85mg/kg)		Journal of Medicinal Chemistry. Vol. 6, Pg. 755, 1963.
mouse	LD50	intravenous	128mg/kg (128mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ANALGESIA	Yakugaku Zasshi. Journal of Pharmacy. Vol. 91, Pg. 550, 1971.
mouse	LD50	subcutaneous	541mg/kg (541mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ANALGESIA	Yakugaku Zasshi. Journal of Pharmacy. Vol. 91, Pg. 550, 1971.
rabbit	LD50	skin	> 2gm/kg (2000mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: FOOD INTAKE (ANIMAL)	National Technical Information Service. Vol. OTS0570591,
rat	LDLo	oral	500mg/kg (500mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: FOOD INTAKE (ANIMAL) GASTROINTESTINAL: OTHER CHANGES	National Technical Information Service. Vol. OTS0570591,

Product Name

Hinokitiol

Synthetic route

Hinokitiol Consensus Reports

Hinokitiol Specification

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