Ascaridole supplier | CasNO.512-85-6

Name
ASCARIDOLE
EINECS 208-147-4
CAS No. 512-85-6
Article Data107
CAS DataBase
Density 1.051 g/cm³
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
Appearance
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
Molecular Structure
Hazard Symbols
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
PSA 18.46000
LogP 2.45170

Synthetic route

: 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene

: 512-85-6
ascaridole

Conditions

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

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%

...Expand

: 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene

A: 512-85-6
ascaridole

B: 99-87-6
4-methylisopropylbenzene

Conditions

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

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

Conditions	Yield
With oxygen In acetone at -5℃; for 0.25h; Product distribution; Irradiation; Rose Bengal sensitizer;	A 15% B 38% C n/a

...Expand

: 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

D: 3-methyl-6-(1-methylethenyl)-7-oxabicyclo<4.1.0>oct-2-one

Conditions

Conditions	Yield
With oxygen In acetone at -5℃; for 0.25h; Irradiation;

...Expand

: 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene

: 807306-71-4
3,7-bis(dimethylamine)phenothiazonium

: 67-63-0
isopropyl alcohol

oxygen: oxygen

: 512-85-6
ascaridole

Conditions

Conditions	Yield
Irradiation;

...Expand

: 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene

: 15086-94-9
eosin y

: 67-63-0
isopropyl alcohol

oxygen: oxygen

: 512-85-6
ascaridole

Conditions

Conditions	Yield
Irradiation;

...Expand

: 67-56-1
methanol

: 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene

rose-bengal: rose-bengal

: 512-85-6
ascaridole

Conditions

Conditions	Yield
at 15℃; Kinetics;

...Expand

: 99-87-6
4-methylisopropylbenzene

: 512-85-6
ascaridole

Conditions

Conditions	Yield
With sodium molybdate; sodium dodecyl-sulfate; butan-1-ol In ethyl acetate at 25℃;

: 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene

A: 512-85-6
ascaridole

B: 99-87-6
4-methylisopropylbenzene

C: 536-66-3
4-Isopropylbenzoic acid

D: 122-03-2
(4-isopropylbenzaldehyde)

Conditions

Conditions	Yield
With oxygen In acetonitrile at 20℃; under 760.051 Torr; for 6h; Catalytic behavior; Irradiation;

...Expand

: 512-85-6
ascaridole

: 1619-26-7, 17948-59-3, 104975-22-6, 123285-71-2
cis-isoascaridole

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene for 18h; Reflux;	85%

: 512-85-6
ascaridole

: 5718-73-0
1-isopropyl-4-methyl-2,3-dioxabicyclo[2,2,2]octane

Conditions

Conditions	Yield
With hydrazinium carbazate; dihydrogen peroxide In tetrahydrofuran; ethanol; water at 20℃; for 12h;	72%
With ethanol; platinum Hydrogenation;

: 512-85-6
ascaridole

: 1619-26-7, 17948-59-3, 104975-22-6, 123285-71-2
cis-isoascaridole

B: 17429-02-6
4-hydroxy-4-methylcyclohexanone

C: 4031-37-2, 10219-66-6, 21473-37-0, 40735-19-1, 94492-01-0
1α,4β-dihydroxymenth-2-ene

D: 70150-56-0
(+/-)-4-hydroxy-4-methyl-2-cyclohexen-1-one

Conditions

Conditions	Yield
With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 25℃; for 42h;	A 68% B 7% C 17% D 7%
With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 25℃; for 42h; Title compound not separated from byproducts;	A 68% B 7% C 17% D 7%

...Expand

: 512-85-6
ascaridole

: 40735-19-1
1,4-dihydroxy-p-menth-2-ene

Conditions

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran for 2.5h; Heating;	50%

: 512-85-6
ascaridole

: 637-88-7
1,4-Cyclohexanedione

: C16H24O4

: C16H24O4

: C16H22O4

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 2h;	A 26% B n/a C n/a

...Expand

: 512-85-6
ascaridole

: 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene

Conditions

Conditions	Yield
With tin(ll) chloride In dichloromethane for 21h; Ambient temperature;	25%

: 512-85-6
ascaridole

: 79099-07-3
N-tert-butyloxycarbonylpiperidin-4-one

: C20H33NO5

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -20℃; for 2.25h;	16%

: 4125-54-6
2-allylphenyl acetate

: 512-85-6
ascaridole

: 67-66-3
chloroform

: 493-08-3
chromane

Conditions

Conditions	Yield
Einleiten von HBr; Kochen des Reaktionsprodukts mit aethanol. KOH;

...Expand

: 512-85-6
ascaridole

: 504-61-0
(E)-but-2-enol

: 507-09-5
thioacetic acid

A: 79473-58-8
thioacetic acid S-(3-hydroxy-1-methyl-propyl ester)

B: 90113-75-0
1-acetoxy-3-acetylsulfanyl-butane

C: bis-(3-acetoxy-1-methyl-propyl)-disulfide

...Expand

: 512-85-6
ascaridole

: 60-29-7
diethyl ether

: 75-16-1
methylmagnesium bromide

A: 34557-54-5
methane

B: 74-84-0
ethane

C: 99-87-6
4-methylisopropylbenzene

...Expand

: 512-85-6
ascaridole

: 618-34-8
1-chlorostyrene

: 612-71-5
1,3,5-triphenylbenzene

Conditions

Conditions	Yield
at 130 - 140℃;

: 512-85-6
ascaridole

: 99-87-6
4-methylisopropylbenzene

2,3-dimethyl-2,3-di-p-tolyl-butane: 2,3-dimethyl-2,3-di-p-tolyl-butane

: 512-85-6
ascaridole

: 68-11-1
mercaptoacetic acid

: 99186-25-1
NSC158362

: 512-85-6
ascaridole

: 107-03-9
1-thiopropane

: 292638-85-8
acrylic acid methyl ester

A: 50354-50-2
3-propylsulfanyl-propionic acid methyl ester

B: 2-(propylsulfanyl-methyl)-glutaric acid dimethyl ester

Conditions

Conditions	Yield
mit UV-Licht.Irradiation;

...Expand

: 512-85-6
ascaridole

: 292638-85-8
acrylic acid methyl ester

: 75-08-1
ethanethiol

A: 18673-13-7
3-ethylsulfanylpropionic acid methyl ester

B: 91007-70-4
2-(ethylsulfanyl-methyl)-glutaric acid dimethyl ester

Conditions

Conditions	Yield
mit UV-Licht.Irradiation;

...Expand

: 512-85-6
ascaridole

: 100-53-8
phenylmethanethiol

: 471-25-0
Propiolic acid

A: 13831-02-2
3-(Z)-(benzylsulfanyl)propenoic acid

B: 13831-01-1
3-(benzylthio)acrylic acid

...Expand

: 512-85-6
ascaridole

: 1745-81-9
2-Allylphenol

: 1746-11-8
2-methyl-2,3-dihydro-1-benzofuran

Conditions

Conditions	Yield
at 100℃;

: 512-85-6
ascaridole

: 187737-37-7
propene

: 75-08-1
ethanethiol

: 4110-50-3
ethyl propyl sulfide

Conditions

Conditions	Yield
at 180℃;

...Expand

: 512-85-6
ascaridole

: 507-09-5
thioacetic acid

: 513-42-8
3-hydroxy-2-methyl-1-propene

: thioacetic acid S-(γ-hydroxy-isobutyl ester)

...Expand

: 512-85-6
ascaridole

: 2,3-dibromo-1,4-epidioxy-p-menthane

Conditions

Conditions	Yield
With bromine; acetic acid

: 512-85-6
ascaridole

: 110-53-2
1-Bromopentane

Conditions

Conditions	Yield
ohne Loesungsmittel;
With pentane

: 512-85-6
ascaridole

A: 3901-93-7, 3901-95-9, 21129-27-1
1-methyl-4-(1-methylethyl)cyclohexanol

B: 91008-90-1
terpin-4-ol

Conditions

Conditions	Yield
With hydrogen; palladium

: 512-85-6
ascaridole

: 91008-90-1
terpin-4-ol

Conditions

Conditions	Yield
With water; hydrogen
With methanol; hydrogen
With water; hydrogen weiteres Reagens: Palladium;
With methanol; hydrogen weiteres Reagens: Palladium;

: 512-85-6
ascaridole

: 856202-99-8
p-menthane-1,2,3,4-tetraol

Conditions

Conditions	Yield
With 4-methylisopropylbenzene at 150℃; man behandelt das Reaktionsprodukt mit Schwefelsaeure bei 20grad;

: 512-85-6
ascaridole

: 6790-83-6
1,4-epoxy-p-menthane-2,3-diol

Conditions

Conditions	Yield
With iron(II) sulfate

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).

Product Name

ASCARIDOLE

Synthetic route

Ascaridole Chemical Properties

Ascaridole History

Ascaridole Uses

Ascaridole Toxicity Data With Reference

Ascaridole Safety Profile

Ascaridole Standards and Recommendations

Ascaridole Specification

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