CAS No.499-44-5,Hinokitiol Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	499-44-5
Name:	Hinokitiol
Article Data:	24

Formula:	C₁₀H₁₂O₂
Molecular Weight:	164.204
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;
EINECS:	207-880-7
Density:	1.127 g/cm³
Melting Point:	50-52 °C
Boiling Point:	303.4 °C at 760 mmHg
Flash Point:	128.1 °C
Solubility:	insoluble in water
Hazard Symbols:	Xn
Risk Codes:	22
Safety:	36
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

Raw Materials

Downstream Products

142-29-0

79-31-2

499-44-5

931-88-4

Total:146 Page 1 of 4 1 2 3 4 Next>>

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Consensus Reports

Reported in EPA TSCA Inventory.

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,