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Guaiazulene
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Name

Guaiazulene

 EINECS 207-701-2
CAS No. 489-84-9 Density 0.976
PSA 0.00000 LogP 4.53160
Solubility Melting Point 28 - 30 C
Formula C15H18 Boiling Point 153 °C7 mm Hg(lit.)
Molecular Weight 198.308 Flash Point 113 ºC
Transport Information 20kgs Appearance dark blue semi-solid
Safety Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes. Risk Codes R22   
Molecular Structure Molecular Structure of 489-84-9 (Guaiazulene) Hazard Symbols
Synonyms

Azulene,7-isopropyl-1,4-dimethyl- (8CI); 1,4-Dimethyl-7-(1-methylethyl)Azulene;1,4-Dimethyl-7-isopropylazulene; 3,8-Dimethyl-5-(2-propyl)azulene;7-Isopropyl-1,4-dimethylazulene; AZ 8; AZ 8 Beris; Azulen-Beris; Azulon;Azunol; Cuteazul; Eucazulen; Guaiazulene; Guaiazulene blue; Kessazulen; NSC4714; Purazulen; S-Guaiazulene; Silazulon; Uroazulen; Vaumigan; Vetivazulen

Article Data 93

Guaiazulene Synthetic route

1203707-11-2

1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}-2-(3-guaiazulenyl)ethylene

275-51-4

azulene

A

489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

1314045-03-8

2-(azulen-1-yl)-1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}ethylene

Conditions
ConditionsYield
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h;A 97%
B 58%
867380-19-6

1-chloro-7-isopropyl-4-methyl-azulene

13061-96-6

dihydroxy-methyl-borane

489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
With palladium diacetate; potassium phosphate In toluene at 100℃; for 24h;94%
275-51-4

azulene

741737-71-3

1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene

A

489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

1314045-02-7

1,3-bis[2,2-bis(4-methoxyphenyl)ethenyl]azulene

C

2-(azulen-1-yl)-1,1-bis(4-methoxyphenyl)ethylene

Conditions
ConditionsYield
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h;A 93%
B 19%
C 34%
1103995-55-6

1,1-bis[4-(dimethylamino)phenyl]-2-(3-guaiazulenyl)ethylene

275-51-4

azulene

A

489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

1314044-93-3

2-(azulen-1-yl)-1,1-bis[4-(dimethylamino)phenyl]ethylene

C

1314044-97-7

1,1-di(azulen-1-yl)-2,2-bis[4-(dimethylamino)phenyl]ethane

D

1314044-96-6

1,3-bis{2,2-bis[4-(dimethylamino)phenyl]ethenyl}azulene

Conditions
ConditionsYield
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h;A 91%
B 46%
C 13%
D 19%
...Expand

dimethyl 3-isopropyl-6,11-dimethyltricyclo<6.2.2.01,7>dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylate

A

489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

98525-07-6, 72898-39-6, 98525-12-3, 98525-13-4

dimethyl 1,6-dimethyl-9-(1-methylethyl)heptalene-4,5-dicarboxylate

Conditions
ConditionsYield
In acetonitrile at 110℃; for 1h;A 29%
B 71%
In acetonitrile at 100℃; for 1h; in sealed tube;A 29%
B 71%

3-bromoguaiazulenium bromide

A

489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

17509-79-4

2,2'-biguaiazulenyl

Conditions
ConditionsYield
With methanol Title compound not separated from byproducts;A 50%
B 20%
64-17-5

ethanol

10487-58-8

bis(3,8-dimethyl-5-isopropyl-1-azulenyl) ketone

A

489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

81920-91-4

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 0.166667h; Heating;
With toluene-4-sulfonic acid for 0.166667h; Mechanism; Heating; regioselectivity; other substrates;
64-17-5

ethanol

150985-85-6

Azulen-1-yl-(5-isopropyl-3,8-dimethyl-azulen-1-yl)-methanone

A

489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

1206-88-8

ethyl azulene-1-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 6h; Heating;
64-17-5

ethanol

150985-81-2

(5-Isopropyl-3,8-dimethyl-azulen-1-yl)-(4,6,8-trimethyl-azulen-1-yl)-methanone

A

489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

81920-91-4

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate

C

4,6,8-Trimethyl-azulene-1-carboxylic acid ethyl ester

D

275-51-4

azulene

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 0.166667h; Heating;
...Expand
64-17-5

ethanol

150985-82-3

1-[3-(5-Isopropyl-3,8-dimethyl-azulene-1-carbonyl)-4,6,8-trimethyl-azulen-1-yl]-ethanone

A

489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

834-97-9

1-acetyl-4,6,8-trimethylazulene

C

81920-91-4

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate

D

3-Acetyl-4,6,8-trimethyl-azulene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 1h; Heating;
...Expand

Guaiazulene Chemical Properties

Chemical Name: Guaiazulene
IUPAC NAME: 1,4-Dimethyl-7-propan-2-ylazulene
CAS No.: 489-84-9
EINECS: 207-701-2
RTECS: CO4790000
Molecular Formula: C15H18
Molecular Weight: 198.3 g/mol
Melting Point: 27-29 °C(lit.)
Density: 0.961 g/cm3 
Flash Point: 142.3 °C
Boiling Point: 305.4 °C at 760 mmHg
Following is the structure of Guaiazulene (489-84-9):


Product Categories about Guaiazulene (489-84-9) are Azulenes ; Biochemistry ; Terpenes ; Terpenes (Others) ; Tropolones & Azulenes
The chemical synonymous of Guaiazulene (489-84-9) are 1,4-Dimethyl-7-(1-methylethyl)-azulen ; 1,4-Dimethyl-7-(1-methylethyl)azulene ; 1,4-Dimethyl-7-(1-methylethyl)-azulene ; 1,4-Dimethyl-7-isopropyl-azulen ; 3,8-Dimethyl-5-(2-propyl)azulene ; AZ-8 ; AZ-8 beris ; Azulen-Beris

Guaiazulene Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 525mg/kg (525mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 54, Pg. 362, 1958.
mouse LD50 oral 1220mg/kg (1220mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 54, Pg. 362, 1958.
rat LD50 oral 1550mg/kg (1550mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 615, 1969.

Guaiazulene Consensus Reports

Reported in EPA TSCA Inventory.

Guaiazulene Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:
Xn: Harmful
Risk Statements about Guaiazulene (489-84-9):
R22 Harmful if swallowed.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements about Guaiazulene (489-84-9):
S22 Do not breathe dust. 
S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection. 
Attentions:
1. Storage: Keep container closed when not in use. Refrigerator (approx 4 °C). Store in a cool, dry area away from incompatible substances.
2. Handling: Do not get in eyes, on skin, or on clothing. Do not ingest or inhale. Do not breathe dust. Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation

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