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Cas Database |
| Name |
Ascaridole |
EINECS | 208-147-4 |
| CAS No. | 512-85-6 | Density | 1.051 g/cm3 |
| PSA | 18.46000 | LogP | 2.45170 |
| Solubility | insoluble in water | Melting Point |
3.3ºC |
| Formula | C10H16 O2 | Boiling Point | 172.3 °C at 760 mmHg |
| Molecular Weight | 168.236 | Flash Point | 55.9 °C |
| Transport Information | N/A | Appearance | N/A |
| Safety | Poison by ingestion. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. Flammable by spontaneous chemical reaction. An oxidizer. Explodes when heated >130° or when exposed to organic acids. Dangerous; heating emits toxic fumes and may explode; reacts with reducing materials. See also CHENOPODIUM OIL and PEROXIDES, ORGANIC. | Risk Codes | N/A |
| Molecular Structure |
|
Hazard Symbols | N/A |
| Synonyms |
p-Menth-2-ene,1,4-epidioxy- (7CI,8CI); 1,4-Peroxido-p-menthene-2; 1,4-Peroxy-p-menth-2-ene;Ascaricum; Ascaridol; Ascaridole; Ascarisin; Askaridol; Boldo ascaridole; NSC406266; NSC 406924 |
Article Data | 107 |
Ascaridole Synthetic route
| Conditions | Yield |
|---|---|
| With oxygen In liquid sulphur dioxide at -72℃; for 4.25h; protected from light; | 99% |
| With sulfur dioxide; oxygen at -72℃; for 4.25h; Product distribution; Mechanism; var. time, var. temp.; | 99% |
| With 5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrin; air In chloroform at 20℃; for 2h; Irradiation; | 99% |
- 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene
A
- 512-85-6
ascaridole
- 114564-48-6, 114618-55-2
2-Isopropyl-5-methyl-cyclohexa-2,5-dienyl-hydroperoxide
C
- 133213-20-4
3-Isopropyl-6-methylene-cyclohex-2-enyl-hydroperoxide
D
- 133213-19-1
5-Isopropyl-2-methyl-cyclohexa-2,5-dienyl-hydroperoxide
| Conditions | Yield |
|---|---|
| With 2,6-di-tert-butyl-4-methyl-phenol; oxygen; rose bengal In methanol for 0.666667h; | A 90% B 2.2% C 0.5% D 2.2% |
| Conditions | Yield |
|---|---|
| With dihydrogen peroxide In dichloromethane at 20℃; for 3h; Solvent; | A 80% B n/a |
| With 5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrin; sodium hydrogencarbonate In chloroform at 20℃; for 7.5h; Irradiation; | A 76% B 24% |
| With 6C16H36N(1+)*2Zn(2+)*4Na(1+)*[Bi2Zn2(ZnW9O34)2](14-); urea hydrogen peroxide adduct In acetonitrile at 70℃; for 24h; Ene Reaction; | A 67% B 37% |
- 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene
A
- 104975-22-6
4-isopropyl-7-methyl-3,8-dioxatricyclo[5.1.0.02,4]octane
B
- 512-85-6
ascaridole
| Conditions | Yield |
|---|---|
| With sodium hydroxide; calcium hypochlorite; dihydrogen peroxide In methanol; water for 24h; | A 15% B 38% |
- 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene
A
- 104975-22-6
4-isopropyl-7-methyl-3,8-dioxatricyclo[5.1.0.02,4]octane
B
- 512-85-6
ascaridole
C
- 99-87-6
4-methylisopropylbenzene
| Conditions | Yield |
|---|---|
| With oxygen In acetone at -5℃; for 0.25h; Product distribution; Irradiation; Rose Bengal sensitizer; | A 15% B 38% C n/a |
- 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene
A
- 104975-22-6
4-isopropyl-7-methyl-3,8-dioxatricyclo[5.1.0.02,4]octane
B
- 512-85-6
ascaridole
C
- 99-87-6
4-methylisopropylbenzene
| Conditions | Yield |
|---|---|
| With oxygen In acetone at -5℃; for 0.25h; Irradiation; |
- 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene
- 807306-71-4
3,7-bis(dimethylamine)phenothiazonium
- 67-63-0
isopropyl alcohol
- 512-85-6
ascaridole
| Conditions | Yield |
|---|---|
| Irradiation; |
- 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene
- 15086-94-9
eosin y
- 67-63-0
isopropyl alcohol
- 512-85-6
ascaridole
| Conditions | Yield |
|---|---|
| Irradiation; |
| Conditions | Yield |
|---|---|
| at 15℃; Kinetics; |
| Conditions | Yield |
|---|---|
| With sodium molybdate; sodium dodecyl-sulfate; butan-1-ol In ethyl acetate at 25℃; |
Ascaridole Chemical Properties
Molecular Formula: C10H16O2
Molar mass: 168.2328 g/mol
EINECS: 200-104-8
Density: 1.051 g/cm3
Flash Point: 55.9 °C
Index of Refraction: 1.498
Boiling Point: 172.3 °C at 760 mmHg
Vapour Pressure:1.78 mmHg at 25 °C
Solubility: Soluble in most organic solvents
Product categories of Ascaridole (CAS NO.512-85-6): Oxidant
Structure of Ascaridole (CAS NO.512-85-6):
XLogP3-AA: 2.3
H-Bond Donor: 0
H-Bond Acceptor: 2
IUPAC Name: 4-Methyl-1-propan-2-yl-7,8-dioxabicyclo[2.2.2]oct-2-ene
Canonical SMILES: CC(C)C12CCC(C=C1)(OO2)C
InChI: InChI=1S/C10H16O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6,8H,5,7H2,1-3H3
InChIKey: MGYMHQJELJYRQS-UHFFFAOYSA-N
Ascaridole History
Ascaridole (CAS NO.512-85-6) was the first and for a long time only discovered naturally occurring organic peroxide. The synthesis started from α-Terpinene which reacts with oxygen under the influence of chlorophyll and light. The structure was resolved by Otto Wallach in 1912, and the first synthesis was done by Karl Ziegler in 1944. Under these conditions singlet oxygen is generated which is reacting in a Diels-Alder reaction with the dien system in the Terpinene.
Ascaridole Uses
Ascaridole (CAS NO.512-85-6) has been used as an anthelmintic for controlling nematodes.
Ascaridole Toxicity Data With Reference
| 1. | skn-rbt 500 mg MLD | SCCUR* Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583) | ||
| 2. | orl-rat LD50:200 mg/kg | FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. 7 (1948),252. | ||
| 3. | orl-mus LD50:400 mg/kg | FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. 7 (1948),252. | ||
| 4. | orl-dog LDLo:250 mg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 24 (1925),359. |
Ascaridole Safety Profile
Poison by ingestion. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. Flammable by spontaneous chemical reaction. An oxidizer. Explodes when heated >130° or when exposed to organic acids. Dangerous; heating emits toxic fumes and may explode; reacts with reducing materials. See also CHENOPODIUM OIL and PEROXIDES, ORGANIC.
Ascaridole Standards and Recommendations
DOT Classification: Forbidden
Ascaridole Specification
Ascaridole ,its cas register number is 512-85-6. It also can be called 2,3-Dioxabicyclo[2.2.2]oct-5-ene, 1-methyl-4- (1-methylethyl)- ; 1-Isopropyl-4-méthyl-2,3-dioxabicyclo[2.2.2]oct-5-ène ; 2,3-Dioxabicyclo[2.2.2]oct-5-ene, 1-isopropyl-4-methyl- and 1-Isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-en . It is a natural organic compound that has an unusual bridging peroxide functional group. Like other low molecular weight organic peroxides, it is unstable and prone to explosion when heated or treated with organic acids. It is the primary constituent of the oil of Mexican Tea (Dysphania ambrosioides, formerly Chenopodium ambrosioides).
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