512-85-6

Basic information

• Product Name: ASCARIDOLE
• Synonyms: 1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo(2.2.2)oct-5-ene;2,3-Dioxabicyclo(2.2.2)oct-5-ene, 1-isopropyl-4-methyl-;Ascaricum;Ascaridiol;Ascaridol;Ascaridole epoxide;Ascarisin;Askaridol
• CAS NO: 512-85-6
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23
• EINECS: 208-147-4
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 512-85-6.mol
• Article Data: 94

Chemical Properties

• Melting Point: 106-107℃ (dec.)
• Boiling Point: 172.3±20.0℃
• Flash Point: 55.9±28.6℃
• Appearance: /
• Density: 1.051±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.78mmHg at 25°C
• Refractive Index: 1.4769 (589.3 nm, 25℃)
• Storage Temp.: Amber Vial, -20?C Freezer
• CAS DataBase Reference: ASCARIDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: ASCARIDOLE(512-85-6)
• EPA Substance Registry System: ASCARIDOLE(512-85-6)

Safety Data

• Hazardous Substances Data: 512-85-6(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Oil

Uses

An organic peroxide which constitutes 60-80% of oil of chenopodium. Anthelmintic.

Definition

ChEBI: A p-menthane monoterpenoid that is p-menth-2-ene with a peroxy group across position 1 to 4.

Hazard

Strong oxidizing agent, explodes on heating to 130C or in contact with organic acids.

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.

InChI:InChI=1/C10H16O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6,8H,5,7H2,1-3H3

Synthetic route

1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) → ascaridole (512-85-6)

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%

1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) → ascaridole (512-85-6) + 2-Isopropyl-5-methyl-cyclohexa-2,5-dienyl-hydroperoxide (114564-48-6, 114618-55-2) + 3-Isopropyl-6-methylene-cyclohex-2-enyl-hydroperoxide (133213-20-4) + 5-Isopropyl-2-methyl-cyclohexa-2,5-dienyl-hydroperoxide (133213-19-1)

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%

1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) → ascaridole (512-85-6) + 4-methylisopropylbenzene (99-87-6)

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%

1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) → 4-isopropyl-7-methyl-3,8-dioxatricyclo[5.1.0.02,4]octane (104975-22-6) + ascaridole (512-85-6)

Conditions	Yield
With sodium hydroxide; calcium hypochlorite; dihydrogen peroxide In methanol; water for 24h;	A 15% B 38%

1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) → 4-isopropyl-7-methyl-3,8-dioxatricyclo[5.1.0.02,4]octane (104975-22-6) + ascaridole (512-85-6) + 4-methylisopropylbenzene (99-87-6)

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

1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) → 4-isopropyl-7-methyl-3,8-dioxatricyclo[5.1.0.02,4]octane (104975-22-6) + ascaridole (512-85-6) + 4-methylisopropylbenzene (99-87-6) + 3-methyl-6-(1-methylethenyl)-7-oxabicyclo<4.1.0>oct-2-one

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

1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + 3,7-bis(dimethylamine)phenothiazonium (807306-71-4) + isopropyl alcohol (67-63-0) + oxygen → ascaridole (512-85-6)

Conditions	Yield
Irradiation;

1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + eosin y (15086-94-9) + isopropyl alcohol (67-63-0) + oxygen → ascaridole (512-85-6)

Conditions	Yield
Irradiation;

methanol (67-56-1) + 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + rose-bengal → ascaridole (512-85-6)

Conditions	Yield
at 15℃; Kinetics;

4-methylisopropylbenzene (99-87-6) → ascaridole (512-85-6)

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

1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) → ascaridole (512-85-6) + 4-methylisopropylbenzene (99-87-6) + 4-Isopropylbenzoic acid (536-66-3) + (4-isopropylbenzaldehyde) (122-03-2)

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

ascaridole (512-85-6) → cis-isoascaridole (1619-26-7, 17948-59-3, 104975-22-6, 123285-71-2)

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

ascaridole (512-85-6) → 1-isopropyl-4-methyl-2,3-dioxabicyclo[2,2,2]octane (5718-73-0)

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

ascaridole (512-85-6) → cis-isoascaridole (1619-26-7, 17948-59-3, 104975-22-6, 123285-71-2) + 4-hydroxy-4-methylcyclohexanone (17429-02-6) + 1α,4β-dihydroxymenth-2-ene (4031-37-2, 10219-66-6, 21473-37-0, 40735-19-1, 94492-01-0) + (+/-)-4-hydroxy-4-methyl-2-cyclohexen-1-one (70150-56-0)

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%

ascaridole (512-85-6) → 1,4-dihydroxy-p-menth-2-ene (40735-19-1)

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

ascaridole (512-85-6) + 1,4-Cyclohexanedione (637-88-7) → C16H24O4 + C16H24O4 + C16H22O4

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

ascaridole (512-85-6) → 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5)

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

ascaridole (512-85-6) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → C20H33NO5

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

2-allylphenyl acetate (4125-54-6) + ascaridole (512-85-6) + chloroform (67-66-3) → chromane (493-08-3)

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

ascaridole (512-85-6) + (E)-but-2-enol (504-61-0) + thioacetic acid (507-09-5) → thioacetic acid S-(3-hydroxy-1-methyl-propyl ester) (79473-58-8) + 1-acetoxy-3-acetylsulfanyl-butane (90113-75-0) + bis-(3-acetoxy-1-methyl-propyl)-disulfide

ascaridole (512-85-6) + diethyl ether (60-29-7) + methylmagnesium bromide (75-16-1) → methane (34557-54-5) + ethane (74-84-0) + 4-methylisopropylbenzene (99-87-6)

ascaridole (512-85-6) + 1-chlorostyrene (618-34-8) → 1,3,5-triphenylbenzene (612-71-5)

Conditions	Yield
at 130 - 140℃;

ascaridole (512-85-6) + 4-methylisopropylbenzene (99-87-6) → 2,3-dimethyl-2,3-di-p-tolyl-butane

ascaridole (512-85-6) + mercaptoacetic acid (68-11-1) → NSC158362 (99186-25-1)

ascaridole (512-85-6) + 1-thiopropane (107-03-9) + acrylic acid methyl ester (292638-85-8) → 3-propylsulfanyl-propionic acid methyl ester (50354-50-2) + 2-(propylsulfanyl-methyl)-glutaric acid dimethyl ester

Conditions	Yield
mit UV-Licht.Irradiation;

ascaridole (512-85-6) + acrylic acid methyl ester (292638-85-8) + ethanethiol (75-08-1) → 3-ethylsulfanylpropionic acid methyl ester (18673-13-7) + 2-(ethylsulfanyl-methyl)-glutaric acid dimethyl ester (91007-70-4)

Conditions	Yield
mit UV-Licht.Irradiation;

ascaridole (512-85-6) + phenylmethanethiol (100-53-8) + Propiolic acid (471-25-0) → 3-(Z)-(benzylsulfanyl)propenoic acid (13831-02-2) + 3-(benzylthio)acrylic acid (13831-01-1)

ascaridole (512-85-6) + 2-Allylphenol (1745-81-9) → 2-methyl-2,3-dihydro-1-benzofuran (1746-11-8)

Conditions	Yield
at 100℃;

ascaridole (512-85-6) + propene (187737-37-7) + ethanethiol (75-08-1) → ethyl propyl sulfide (4110-50-3)

Conditions	Yield
at 180℃;

ascaridole (512-85-6) + thioacetic acid (507-09-5) + 3-hydroxy-2-methyl-1-propene (513-42-8) → thioacetic acid S-(γ-hydroxy-isobutyl ester)

ascaridole (512-85-6) → 2,3-dibromo-1,4-epidioxy-p-menthane

Conditions	Yield
With bromine; acetic acid

ascaridole (512-85-6) → 1-Bromopentane (110-53-2)

Conditions	Yield
ohne Loesungsmittel;
With pentane

ascaridole (512-85-6) → 1-methyl-4-(1-methylethyl)cyclohexanol (3901-93-7, 3901-95-9, 21129-27-1) + terpin-4-ol (91008-90-1)

Conditions	Yield
With hydrogen; palladium

ascaridole (512-85-6) → terpin-4-ol (91008-90-1)

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

ascaridole (512-85-6) → p-menthane-1,2,3,4-tetraol (856202-99-8)

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

ascaridole (512-85-6) → 1,4-epoxy-p-menthane-2,3-diol (6790-83-6)

Conditions	Yield
With iron(II) sulfate

Upstream product

• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 99-87-6 4-methylisopropylbenzene 
• 67-56-1 methanol 
• 15086-94-9 eosin y 
• 67-63-0 isopropyl alcohol 
• 807306-71-4 3,7-bis(dimethylamine)phenothiazonium 

Downstream Products

• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 99-87-6 4-methylisopropylbenzene 
• 1619-26-7 cis-isoascaridole 
• 17429-02-6 4-hydroxy-4-methylcyclohexanone 
• 4031-37-2 1α,4β-dihydroxymenth-2-ene 
• 70150-56-0 (+/-)-4-hydroxy-4-methyl-2-cyclohexen-1-one 
• 4031-37-2 cis-1-isopropyl-4-methylcyclohex-2-ene-1,4-diol 
• 67-63-0 isopropyl alcohol 
• 106-44-5 p-cresol 
• 74-98-6 propane 
• 6790-83-6 (1RS,2RS,3SR)-1,4-epoxy-p-menthane-2,3-diol 
• 64-18-6 formic acid 
• 64-19-7 acetic acid 
• 79-31-2 isobutyric Acid 

Relevant articles and documents

Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H2O2: An Access to Artemisinin

Herein, we report an efficient method for the chemical generation of 1O2 by treatment of H2O2 with AIBX, a highly water-soluble, bench-stable, recyclable hypervalent iodine(V) reagent developed by our group. The generation of 1O2 was confirmed by the following results: (1) capture of 1O2 with the sodium salt of anthracene-9,10-bis(ethanesulfonate) produced the corresponding endoperoxide and (2) TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) produced by the oxidation of 2,2,6,6-tetramethylpiperidine with 1O2 generated using the AIBX/H2O2 system was detected by electron spin resonance spectroscopy. To illustrate the potential utility of this method for organic synthesis, we used the AIBX/H2O2 system to perform typical reactions of 1O2: [2 + 2]/[4 + 2] cycloadditions, Schenck ene reactions, and heteroatom oxidation reactions, which afforded the corresponding products in high yields. Moreover, we used the method to synthesize the antimalarial drug artemisinin. Finally, we demonstrated that AIBX could be regenerated after the reaction by means of a workup involving extraction and removal of water to obtain a precursor of AIBX, which could then be re-oxidized.

8,8′-(Benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(quinolin-4(1H)-one): a twisted photosensitizer with AIE properties

A new benzothiadiazole (BTZ) luminogen is preparedviathe Suzuki-Miyaura Pd-catalysed C-C cross-coupling of 8-iodoquinolin-4(1H)-one and a BTZ bispinacol boronic ester. The rapid reaction (5 min) affords the air-, thermo-, and photostable product in 97% yield as a yellow precipitate that can be isolated by filtration. The luminogen exhibits aggregated-induced emission (AIE) properties, which are attributed to its photoactive BTZ core and nonplanar geometry. It also behaves as a molecular heterogeneous photosensitizer for the production of singlet oxygen under continuous flow conditions.

Singlet-Oxygen Generation by Peroxidases and Peroxygenases for Chemoenzymatic Synthesis

Singlet oxygen is a reactive oxygen species undesired in living cells but a rare and valuable reagent in chemical synthesis. We present a fluorescence spectroscopic analysis of the singlet-oxygen formation activity of commercial peroxidases and novel peroxygenases. Singlet-oxygen sensor green (SOSG) is used as fluorogenic singlet oxygen trap. Establishing a kinetic model for the reaction cascade to the fluorescent SOSG endoperoxide permits a kinetic analysis of enzymatic singlet-oxygen formation. All peroxidases and peroxygenases show singlet-oxygen formation. No singlet oxygen activity could be found for any catalase under investigation. Substrate inhibition is observed for all reactive enzymes. The commercial dye-decolorizing peroxidase industrially used for dairy bleaching shows the highest singlet-oxygen activity and the lowest inhibition. This enzyme was immobilized on a textile carrier and successfully applied for a chemical synthesis. Here, ascaridole was synthesized via enzymatically produced singlet oxygen.