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661-19-8 Usage

Chemical Properties

1-DOCOSANOL is white powder

Uses

Different sources of media describe the Uses of 661-19-8 differently. You can refer to the following data:
1. n-Docosanol is a binder and an emulsion stabilizer. It is also used to increase a formulation’s viscosity. This is a mixture of fatty alcohols. behenyl alcohol may be used for any number of purposes in a cosmetic formulation, including as an emollient, a binder, an emulsion stabilizer, or to increase a product’s viscosity. It may be derived either synthetically or from plants.
2. 1-Docosanol works as a surfactant in cosmetics. 1-Docosanol cream has also been approved by the US Food and Drug Administration as a safe and effective topical treatment for herpes labialis

Indications

Docosanol (Abreva) is a long-chain saturated alcohol that is clinically effective against HSV. It has in vitro activity against many enveloped viruses, including CMV, influenzavirus, and respiratory syncytial virus. Docosanol is not directly virucidal; instead, it blocks the entry of the virion into the host cell by inhibiting the fusion of the viral envelope with the host plasma membrane. Because it does not affect viral replication or protein production, it may be less susceptible to the development of resistance than other antiviral drugs.

Definition

1-DOCOSANOL is a long-chain, saturated fatty alcohol.

General Description

1-Docosanol inhibits replication of certain viruses (herpes simplex virus and respiratory syncytial virus) within primary target cells in vitro. It has been isolated from Clematis brevicaudata.

Flammability and Explosibility

Notclassified

Pharmaceutical Applications

1-DOCOSANOL is a 22-carbon straight chain alcohol licensed for over-thecounter sales for the topical treatment of herpes labialis. It is thought to act by blocking viral fusion with the host cell, although definitive studies are lacking. The clinical relevance of the antiviral activity has been debated and the place of this medication as a treatment of herpes labialis remains to be established.

Clinical Use

Docosanol cream is approved for the over-the-counter treatment of herpes labialis. It shortens the duration of symptoms of cold sores and fever blisters but does not provide symptomatic relief.

Side effects

Adverse effects of docosanol are minimal. Skin irritation occurs infrequently. Drug interactions are not anticipated.

Purification Methods

Crystallise docosanol from ether or chloroform/ether. [Beilstein 1 IV 1906.]

Check Digit Verification of cas no

The CAS Registry Mumber 661-19-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,6 and 1 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 661-19:
(5*6)+(4*6)+(3*1)+(2*1)+(1*9)=68
68 % 10 = 8
So 661-19-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H10BrN/c7-5-3-1-2-4-6-8/h1-5H2

661-19-8 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (D0964)  1-Docosanol  >98.0%(GC)

  • 661-19-8

  • 25g

  • 210.00CNY

  • Detail
  • TCI America

  • (D0964)  1-Docosanol  >98.0%(GC)

  • 661-19-8

  • 500g

  • 995.00CNY

  • Detail
  • Aldrich

  • (169102)  1-Docosanol  98%

  • 661-19-8

  • 169102-50G

  • 724.23CNY

  • Detail

661-19-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Docosanol

1.2 Other means of identification

Product number -
Other names Emery 3304

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:661-19-8 SDS

661-19-8Synthetic route

1-docosanol
42449-18-3

1-docosanol

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With iodine In methanol microwave irradiation;100%
tert-butyl-docosyloxy-dimethyl-silane

tert-butyl-docosyloxy-dimethyl-silane

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With iodine In methanol microwave irradiation;100%
n-docosanal
57402-36-5

n-docosanal

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With magnesium; tin(ll) chloride In tetrahydrofuran for 0.25h;98%
2-Docosyloxy-tetrahydro-pyran
184678-19-1

2-Docosyloxy-tetrahydro-pyran

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With CuCl2*H2O In ethanol for 3h; Hydrolysis; Heating;91%
With iodine In methanol for 0.166667h; microwave irradiation;80%
With toluene-4-sulfonic acid In methanol for 8h; Ambient temperature;
n-docosanoic acid
112-85-6

n-docosanoic acid

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0 - 30℃; Reagent/catalyst;87.6%
Multi-step reaction with 2 steps
1: H2SO4 / 7 h / Heating
2: LiAlH4 / tetrahydrofuran / 3 h / 0 - 20 °C
View Scheme
With acetic acid
icosane
112-95-8

icosane

n-docosane
629-97-0

n-docosane

n-hexacosane
630-01-3

n-hexacosane

Tridecane
629-50-5

Tridecane

octadecane
593-45-3

octadecane

tetracosane
646-31-1

tetracosane

octacosane
630-02-4

octacosane

n-triacontane
638-68-6

n-triacontane

A

1-octadecanol
112-92-5

1-octadecanol

B

n-eicosanol
629-96-9

n-eicosanol

C

melissyl alcohol
593-50-0

melissyl alcohol

D

1-docosanol
661-19-8

1-docosanol

E

tetracosyl alcohol
506-51-4

tetracosyl alcohol

F

hexacosyl alcohol
506-52-5

hexacosyl alcohol

G

octacosyl alcohol
557-61-9

octacosyl alcohol

Conditions
ConditionsYield
Stage #1: icosane; n-docosane; n-hexacosane; octadecane; tetracosane; octacosane; n-triacontane With oxygen at 30 - 50℃; under 1575.16 Torr; for 0.5h;
Stage #2: Tridecane With titanium(IV) isopropylate at 30 - 50℃; under 1575.16 - 3750.38 Torr; for 6.86667h;
Stage #3: With sulfuric acid; water at 80℃; Product distribution / selectivity;
A 17.66%
B 19.46%
C 0.1%
D 13.62%
E 6.93%
F 2.04%
G 0.48%
icosane
112-95-8

icosane

n-docosane
629-97-0

n-docosane

n-hexacosane
630-01-3

n-hexacosane

octadecane
593-45-3

octadecane

tetracosane
646-31-1

tetracosane

octacosane
630-02-4

octacosane

n-triacontane
638-68-6

n-triacontane

A

1-octadecanol
112-92-5

1-octadecanol

B

n-eicosanol
629-96-9

n-eicosanol

C

melissyl alcohol
593-50-0

melissyl alcohol

D

1-docosanol
661-19-8

1-docosanol

E

tetracosyl alcohol
506-51-4

tetracosyl alcohol

F

hexacosyl alcohol
506-52-5

hexacosyl alcohol

G

octacosyl alcohol
557-61-9

octacosyl alcohol

Conditions
ConditionsYield
Stage #1: icosane; n-docosane; n-hexacosane; octadecane; tetracosane; octacosane; n-triacontane With oxygen at 30 - 50℃; under 1575.16 - 3675.37 Torr; for 3h;
Stage #2: With sulfuric acid; water Product distribution / selectivity;
A 12.4%
B 13.4%
C 0.05%
D 7.8%
E 3.2%
F 1%
G 0.2%
ethyl docosanoate
5908-87-2

ethyl docosanoate

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With copper oxide-chromium oxide under 147102 Torr; Hydrogenation;
With lithium aluminium tetrahydride; diethyl ether
docosanoic acid phenyl ester
149068-49-5

docosanoic acid phenyl ester

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With i-Amyl alcohol; sodium
behenic acid methyl ester
929-77-1

behenic acid methyl ester

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3h;
With lithium aluminium tetrahydride In tetrahydrofuran
docosyloxymethylbenzene
197958-45-5

docosyloxymethylbenzene

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With naphthalene; water; lithium 1.) THF, -78 deg C - 20 deg C, 2 h; Yield given. Multistep reaction;
docosyloxydimethylphenylsilane
197958-43-3

docosyloxydimethylphenylsilane

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With naphthalene; water; lithium 1.) THF, 0 deg C, 4 h; Yield given. Multistep reaction;
behenic acid amide

behenic acid amide

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With pentan-1-ol; sodium
behenic acid ethyl ester

behenic acid ethyl ester

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With sodium Darst.;
With sodium; Petroleum ether; butan-1-ol
With pentan-1-ol; sodium
With ethanol; sodium
erucyl alcohol

erucyl alcohol

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
With diethyl ether; hydrogen; platinum
diethyl ether
60-29-7

diethyl ether

13-docosen-1-ol
23519-83-7

13-docosen-1-ol

hydrogen

hydrogen

platinum black

platinum black

1-docosanol
661-19-8

1-docosanol

cis-13-docosenoic acid butyl ester
19773-46-7

cis-13-docosenoic acid butyl ester

zinc chromite

zinc chromite

A

1-docosanol
661-19-8

1-docosanol

B

erucyl alcohol

erucyl alcohol

Conditions
ConditionsYield
at 295℃; under 147102 Torr; Hydrogenation;
methyl cis-13-docosenoate
1120-34-9

methyl cis-13-docosenoate

zinc chromite

zinc chromite

A

(13E)-docos-13-en-1-ol
5634-26-4

(13E)-docos-13-en-1-ol

B

1-docosanol
661-19-8

1-docosanol

C

erucyl alcohol

erucyl alcohol

Conditions
ConditionsYield
at 330 - 335℃; Hydrogenation;
i-Amyl alcohol
123-51-3

i-Amyl alcohol

docosanoic acid phenyl ester
149068-49-5

docosanoic acid phenyl ester

sodium

sodium

1-docosanol
661-19-8

1-docosanol

15-(methoxycarbonyl)pentadecanoic acid
18451-85-9

15-(methoxycarbonyl)pentadecanoic acid

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72 percent / MeONa / methanol / 27 °C / Electrochemical reaction; Pt anode; graphite cathode
2: lithium aluminium hydride / tetrahydrofuran
View Scheme
azelaic monomethyl ester
2104-19-0

azelaic monomethyl ester

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: MeONa / methanol / Electrolysis; Pt anode; graphite cathode
2: Ba(OH)2
3: 72 percent / MeONa / methanol / 27 °C / Electrochemical reaction; Pt anode; graphite cathode
4: lithium aluminium hydride / tetrahydrofuran
View Scheme
dimethyl hexadecanedioate
19102-90-0

dimethyl hexadecanedioate

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Ba(OH)2
2: 72 percent / MeONa / methanol / 27 °C / Electrochemical reaction; Pt anode; graphite cathode
3: lithium aluminium hydride / tetrahydrofuran
View Scheme
2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran
53963-10-3

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) n-BuLi / 1.) THF, hexane, -10 deg C, 3,5 h, 2.) THF, hexane, -10 deg C, 4 h
2: 87 percent / Raney nickel / 5 h / Heating
3: p-toluenesulfonic acid / methanol / 8 h / Ambient temperature
View Scheme
2-pentadecyl-[1,3]dithiane
59014-51-6

2-pentadecyl-[1,3]dithiane

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) n-BuLi / 1.) THF, hexane, -10 deg C, 3,5 h, 2.) THF, hexane, -10 deg C, 4 h
2: 87 percent / Raney nickel / 5 h / Heating
3: p-toluenesulfonic acid / methanol / 8 h / Ambient temperature
View Scheme
n-hexadecylaldehyde
629-80-1

n-hexadecylaldehyde

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) n-BuLi / 1.) THF, hexane, -10 deg C, 45 min, 2.) THF, hexane, room temperature, overnight
2: 86 percent / H2 / Pd/C / methanol / 6 h
3: H2SO4 / 7 h / Heating
4: LiAlH4 / tetrahydrofuran / 3 h / 0 - 20 °C
View Scheme
(5-carboxypentyl)triphenylphosphonium bromide
50889-29-7

(5-carboxypentyl)triphenylphosphonium bromide

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) n-BuLi / 1.) THF, hexane, -10 deg C, 45 min, 2.) THF, hexane, room temperature, overnight
2: 86 percent / H2 / Pd/C / methanol / 6 h
3: H2SO4 / 7 h / Heating
4: LiAlH4 / tetrahydrofuran / 3 h / 0 - 20 °C
View Scheme
6-docosenoic acid
116802-23-4

6-docosenoic acid

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent / H2 / Pd/C / methanol / 6 h
2: H2SO4 / 7 h / Heating
3: LiAlH4 / tetrahydrofuran / 3 h / 0 - 20 °C
View Scheme
2-[6-(2-Pentadecyl-[1,3]dithian-2-yl)-hexyloxy]-tetrahydro-pyran
184678-18-0

2-[6-(2-Pentadecyl-[1,3]dithian-2-yl)-hexyloxy]-tetrahydro-pyran

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 87 percent / Raney nickel / 5 h / Heating
2: p-toluenesulfonic acid / methanol / 8 h / Ambient temperature
View Scheme
1-Bromononane
693-58-3

1-Bromononane

1-docosanol
661-19-8

1-docosanol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran
2: potassium hydride; Trimethylenediamine
3: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran
4: hydrogen
5: hydrogen; palladium 10% on activated carbon / ethyl acetate
View Scheme
1-docosanol
661-19-8

1-docosanol

n-docosanoic acid
112-85-6

n-docosanoic acid

docosyl docosanoate
17671-27-1

docosyl docosanoate

Conditions
ConditionsYield
at 250℃; for 15h; Inert atmosphere;99.6%
With C28H60O3PS(1+)*CF3O3S(1-) at 80℃; for 6h; Sealed tube;
1-docosanol
661-19-8

1-docosanol

acetic anhydride
108-24-7

acetic anhydride

1-docosanol acetate
822-26-4

1-docosanol acetate

Conditions
ConditionsYield
With magnesium(II) perchlorate at 40℃; for 1h;99%
zinc(II) perchlorate In diethyl ether for 30h;99%
phosgene
75-44-5

phosgene

1-docosanol
661-19-8

1-docosanol

1-docosanyl chloroformate
81691-95-4

1-docosanyl chloroformate

Conditions
ConditionsYield
In diethyl ether; dichloromethane; toluene Ambient temperature;98%
In diethyl ether; dichloromethane; toluene98%
1-docosanol
661-19-8

1-docosanol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

docosyl mesylate
123253-22-5

docosyl mesylate

Conditions
ConditionsYield
With triethylamine In dichloromethane97%
With triethylamine In dichloromethane at 20℃; for 3h;
With triethylamine In tetrahydrofuran at 40℃; for 2h; Cooling with ice bath;
With pyridine at 0 - 20℃; for 24h;
1-docosanol
661-19-8

1-docosanol

acrylic acid
79-10-7

acrylic acid

behenyl acrylate
18299-85-9

behenyl acrylate

Conditions
ConditionsYield
With 10H-phenothiazine; hydroquinone at 110 - 130℃; for 4.5h;95.8%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

1-docosanol
661-19-8

1-docosanol

2-Docosyloxy-tetrahydro-pyran
184678-19-1

2-Docosyloxy-tetrahydro-pyran

Conditions
ConditionsYield
With iodine In tetrahydrofuran for 0.133333h; microwave irradiation;95%
1-docosanol
661-19-8

1-docosanol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyl-docosyloxy-dimethyl-silane

tert-butyl-docosyloxy-dimethyl-silane

Conditions
ConditionsYield
With iodine In 1,2-dichloro-ethane at 71 - 72℃; for 0.0333333h; microwave irradiation;95%
nonanoic acid
112-05-0

nonanoic acid

1-docosanol
661-19-8

1-docosanol

nonanoic acid docosyl ester

nonanoic acid docosyl ester

Conditions
ConditionsYield
With magnesium sulfate; zinc(II) perchlorate at 80℃; for 12h;95%
1-docosanol
661-19-8

1-docosanol

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

docosanyl palmitate
42232-33-7

docosanyl palmitate

Conditions
ConditionsYield
With choline chloride; zinc(II) chloride at 110℃; for 12h;95%
1-docosanol
661-19-8

1-docosanol

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

docosyl 4-methylbenzoate
1036648-35-7

docosyl 4-methylbenzoate

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine In dichloromethane at -78℃; for 0.5h;94%
With N,N,N,N,-tetramethylethylenediamine In dichloromethane at -78℃; for 0.5h; Inert atmosphere;94%
With N,N,N,N,-tetramethylethylenediamine In dichloromethane at -78℃; for 0.5h; Inert atmosphere;94%
2,2-dimethyl-3-hydroxypropyl 2-cyano-3,3-diphenylpropenoate

2,2-dimethyl-3-hydroxypropyl 2-cyano-3,3-diphenylpropenoate

1-docosanol
661-19-8

1-docosanol

Reaxys ID: 15740702

Reaxys ID: 15740702

Conditions
ConditionsYield
Stage #1: poly(octadecene-1-co-maleic anhydride) resin; 2,2-dimethyl-3-hydroxypropyl 2-cyano-3,3-diphenylpropenoate; TYZOR DEA In xylene for 18h; Heating / reflux;
Stage #2: 1-docosanol; TYZOR DEA In xylene for 8h; Heating / reflux;
93%
diaminodecane
646-25-3

diaminodecane

1-docosanol
661-19-8

1-docosanol

Hexamethylene diisocyanate
822-06-0

Hexamethylene diisocyanate

C70H140N6O6

C70H140N6O6

Conditions
ConditionsYield
Stage #1: 1-docosanol; Hexamethylene diisocyanate; dibutyltin dilaurate In tetrahydrofuran; hexane at 20 - 60℃; for 1h;
Stage #2: diaminodecane In tetrahydrofuran; hexane at 20℃; for 1h;
93%
1-docosanol
661-19-8

1-docosanol

1,2-bis(5-(2-carboxyethyl)-3-methyl-2-thienyl)hexafluorocyclopentene
1609928-88-2

1,2-bis(5-(2-carboxyethyl)-3-methyl-2-thienyl)hexafluorocyclopentene

1,2-bis(5-(2-(docosyloxycarbonyl)ethyl)-3-methyl-2-thienyl)perfluorocyclopentene

1,2-bis(5-(2-(docosyloxycarbonyl)ethyl)-3-methyl-2-thienyl)perfluorocyclopentene

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 72h;93%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

1-docosanol
661-19-8

1-docosanol

1-docosanol
42449-18-3

1-docosanol

Conditions
ConditionsYield
With iodine In 1,2-dichloro-ethane at 46 - 50℃; for 0.0333333h; microwave irradiation;92%
Adipic acid
124-04-9

Adipic acid

1-docosanol
661-19-8

1-docosanol

di-behenyl adipate
65540-77-4

di-behenyl adipate

Conditions
ConditionsYield
With choline chloride; zinc(II) chloride at 110℃; for 24h;92%
1-docosanol
661-19-8

1-docosanol

n-docosane
629-97-0

n-docosane

Conditions
ConditionsYield
With 4-methyl-benzoic acid methyl ester; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 60℃; for 6h; Electrolysis; Inert atmosphere;92%
Multi-step reaction with 2 steps
1: phosphorus; iodine
2: zinc; hydrochloric acid; glacial acetic acid
View Scheme
1-docosanol
661-19-8

1-docosanol

1-Bromodocosane
6938-66-5

1-Bromodocosane

Conditions
ConditionsYield
With phosphorus tribromide In dichloromethane at 100℃; for 4h; Inert atmosphere;91.2%
With N-Bromosuccinimide; potassium hexamethylsilazane; (1,3,4)-triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-ylidene In dichloromethane at 20℃; for 6h; Reagent/catalyst; Appel Halogenation; Inert atmosphere;77%
With hydrogen bromide at 150℃;
tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate
910803-59-7

tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate

1-docosanol
661-19-8

1-docosanol

tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)tetracosanoate

tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)tetracosanoate

Conditions
ConditionsYield
With triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine In toluene at 0 - 20℃; for 12h; Reagent/catalyst; Mitsunobu Displacement;91%
1-docosanol
661-19-8

1-docosanol

n-docosanal
57402-36-5

n-docosanal

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane at 20℃; for 6h; Molecular sieve; Inert atmosphere;88%
With N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate In dichloromethane; water at 20℃; for 20h; Inert atmosphere;86%
With pyridinium chlorochromate In dichloromethane at 20℃; for 6h;83%
vinylsulfonyl chloride
6608-47-5

vinylsulfonyl chloride

1-docosanol
661-19-8

1-docosanol

docosyl ethenesulfonate
75391-27-4

docosyl ethenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane for 0.166667h;88%
1-docosanol
661-19-8

1-docosanol

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

4'-hydroxy-trans-cinnamic acid docosyl ester
101959-29-9

4'-hydroxy-trans-cinnamic acid docosyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;88%
With toluene-4-sulfonic acid In acetone; benzene at 80℃; for 2h; Yield given;
1-docosanol
661-19-8

1-docosanol

[4-(7-Diethylamino-2-oxo-2H-chromen-3-yl)-phenyl]-oxo-acetonitrile
203256-20-6

[4-(7-Diethylamino-2-oxo-2H-chromen-3-yl)-phenyl]-oxo-acetonitrile

4-(7-Diethylamino-2-oxo-2H-chromen-3-yl)-benzoic acid docosyl ester

4-(7-Diethylamino-2-oxo-2H-chromen-3-yl)-benzoic acid docosyl ester

Conditions
ConditionsYield
With dmap In acetonitrile for 1.5h; Heating;88%
1-docosanol
661-19-8

1-docosanol

Dibenzyl N,N-diisopropylphosphoramidite
108549-23-1

Dibenzyl N,N-diisopropylphosphoramidite

phosphoric Acid dibenzyl ester docosanyl ester
80078-48-4

phosphoric Acid dibenzyl ester docosanyl ester

Conditions
ConditionsYield
Stage #1: 1-docosanol; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole In dichloromethane at 25℃; for 2h;
Stage #2: With peracetic acid In dichloromethane at -38 - 0℃;
88%
1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

1-docosanol
661-19-8

1-docosanol

di-behenyl sebacate
42233-75-0

di-behenyl sebacate

Conditions
ConditionsYield
With choline chloride; zinc(II) chloride at 110℃; for 24h;88%
1-docosanol
661-19-8

1-docosanol

phosphoric Acid dibenzyl ester docosanyl ester
80078-48-4

phosphoric Acid dibenzyl ester docosanyl ester

Conditions
ConditionsYield
88%
88%
1-docosanol
661-19-8

1-docosanol

3-(4-hydroxyphenyl)prop-2-yn-1-oic acid
78589-65-8

3-(4-hydroxyphenyl)prop-2-yn-1-oic acid

C31H50O3
1173709-64-2

C31H50O3

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h;88%

661-19-8Relevant articles and documents

Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities

Fernández Montoya, Deicy J.,Contreras Jordan, Luis A.,Moreno-Murillo, Bárbara,Silva-Gómez, Edelberto,Mayorga-Wandurraga, Humberto

supporting information, p. 2544 - 2550 (2019/11/13)

Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2S. Three AKGs (5l–5n) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (5a–5k, 5o). Their structures were established using 1H and 13C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs 5a–5m and 5o showed activity against five clinical isolates and P. aeruginosa ATCC 15442, with MIC values in the range of 15–125 μg/mL. In addition, at half of the MIC, most of the AKGs reduced S. aureus biofilm formation in the range of 23%–99% and P. aeruginosa ATCC 15442 biofilm formation in the range of 14%–64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.

Novel Process for the Synthesis of Docosanol

-

, (2019/06/15)

The present invention relates to a novel process for the preparation of Docosanol (I). More particularly, the invention relates to a novel process for the preparation of Docosanol (I) in a substantially pure form with a purity level of greater than 99.5%. The invention also relates to novel crystalline forms of Docosanol (I) and process for preparation thereof.

Synthesis of long-chain fatty acid derivatives as a novel anti-Alzheimer's agent

Zhang, Hong-Yan,Yamakawa, Yu-Ichiro,Matsuya, Yuji,Toyooka, Naoki,Tohda, Chihiro,Awale, Suresh,Li, Feng,Kadota, Shigetoshi,Tezuka, Yasuhiro

, p. 604 - 608 (2014/01/23)

In order to develop new drugs for Alzheimer's disease, we prepared 17 fatty acid derivatives with different chain lengths and different numbers and positions of double bonds by using Wittig reaction and stereospecific hydrogenation of triple bonds as key reactions. Among them, (4Z,15Z)- octadecadienoic acid (10) and (23Z,34Z)-heptatriacontadienoic acid (16) showed the most potent neurite outgrowth activities on Aβ(25-35)-treated rat cortical neurons, which activities were comparable to that of a positive control, NGF. Both fatty acids 10 and 16 possess two (Z)-double bonds at the n-3 and n-14 positions, which might be important for the neurite outgrowth activity.

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