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112-53-8 Usage

Chemical Properties

Lauryl alcohol has a characteristic fatty odor; unpleasant at high concentrations, but delicate and floral on dilution. 1-Dodecanol is a saturated 12-carbon fatty alcohol obtained from coconut oil fatty acids. It has a fatty, waxy flavor and is used in detergents, lubricating oils, and pharmaceuticals.

Physical properties

1-Dodecanol is a white low melting crystalline solid that has a melting point of 24°C.The air odor threshold for dodecyl alcohol (isomer not specified) is reported to be 7.1 ppb.

Occurrence

Reported found in the oil of Mexican lime and in the oil from flowers of Furcraea gigantean. Also reported found in apple, banana, sour cherry, citrus peel oils, melon, pineapple, potato, thymus, cheeses, butter, milk powder, chicken and beef fat, cooked pork, beer, whiskies, white wine, peanuts, beans, mushrooms, mango, coriander seed and leaf, rice, Bourbon vanilla, endive, crab, clam, Cape gooseberry, pawpaw and maté.

Uses

Different sources of media describe the Uses of 112-53-8 differently. You can refer to the following data:
1. 1-Dodecanol is used as a cosmetic, textile auxiliaries, synthetic oil, emulsifiers and flotation agent of raw materials, a detergent raw material, a foaming agent of the toothpaste.
2. 1-Dodecanol is used in chemical formulations for a variety of purposes, including as an emulsion stabilizer, a skin-conditioning emollient, and a viscosity-increasing agent.

Definition

ChEBI: 1-Dodecanol is a fatty alcohol that is dodecane in which a hydrogen from one of the methyl groups is replaced by a hydroxy group. It is registered for use in apple and pear orchards as a Lepidopteran pheromone/sex attractant, used to disrupt the mating behaviour of certa n moths whose larvae destroy crops.

Preparation

Commercially 1-Dodecanol may be prepared by hydrogenation of lauric acid; normally employed as a replacement for the corresponding aldehyde.

Production Methods

1-Dodecanol is produced commercially by the oxo process and from ethylene by the Ziegler process, which involves oxidation of trialkylaluminum compounds. It can also be produced by sodium reduction or high-pressure hydrogenation of esters of naturally occurring lauric acid.

Aroma threshold values

Detection: 73 to 820 ppb

Synthesis Reference(s)

Journal of the American Chemical Society, 108, p. 6036, 1986 DOI: 10.1021/ja00279a061Tetrahedron Letters, 37, p. 3623, 1996 DOI: 10.1016/0040-4039(96)00652-1

General Description

Colorless thick liquid with a sweet odor. Floats on water. Freezing point is 75°F.

Reactivity Profile

Dodecyl alcohol is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Health Hazard

Liquid will cause burning of the eyes and may irritate skin.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. A severe human skin irritant. Questionable carcinogen with experimental tumorigenic data. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use dry chemical, CO2. When heated to decomposition it emits acrid smoke and irritating fumes

Carcinogenicity

1-Dodecanol showed weak tumor-promoting activity when applied three times a week for 60 weeks to the skin of mice that had previously received an initiating dose of dimethylbenz[a]anthracene. Papillomas developed in 2 of 30 mice after 39 and 49 weeks of treatment.

Purification Methods

Crystallise dodecanol from aqueous EtOH, and distil it through a spinning-band column under vacuum. [Ford & Marvel Org Synth 10 62 1930, Beilstein 1 IV 1844.]

Check Digit Verification of cas no

The CAS Registry Mumber 112-53-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 2 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 112-53:
(5*1)+(4*1)+(3*2)+(2*5)+(1*3)=28
28 % 10 = 8
So 112-53-8 is a valid CAS Registry Number.
InChI:InChI=1/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3

112-53-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • USP

  • (1356891)  Laurylalcohol  United States Pharmacopeia (USP) Reference Standard

  • 112-53-8

  • 1356891-125MG

  • 4,647.24CNY

  • Detail
  • Sigma-Aldrich

  • (443816)  1-Dodecanol  ACS reagent, ≥98.0%

  • 112-53-8

  • 443816-500G

  • 848.25CNY

  • Detail
  • Sigma-Aldrich

  • (443816)  1-Dodecanol  ACS reagent, ≥98.0%

  • 112-53-8

  • 443816-1KG

  • 1,407.51CNY

  • Detail
  • Sigma-Aldrich

  • (44095)  1-Dodecanol  Selectophore, ≥98.0%

  • 112-53-8

  • 44095-1G

  • 380.25CNY

  • Detail
  • Sigma-Aldrich

  • (44095)  1-Dodecanol  Selectophore, ≥98.0%

  • 112-53-8

  • 44095-25G

  • 4,015.44CNY

  • Detail
  • Vetec

  • (V900234)  1-Dodecanol  Vetec reagent grade, 98%

  • 112-53-8

  • V900234-500ML

  • 133.38CNY

  • Detail
  • Sigma-Aldrich

  • (126799)  1-Dodecanol  reagent grade, 98%

  • 112-53-8

  • 126799-250ML

  • 155.61CNY

  • Detail
  • Sigma-Aldrich

  • (126799)  1-Dodecanol  reagent grade, 98%

  • 112-53-8

  • 126799-1L

  • 238.68CNY

  • Detail

112-53-8SDS

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 dodecan-1-ol

1.2 Other means of identification

Product number -
Other names Dodecyl Alcohol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances;Solvents
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:112-53-8 SDS

112-53-8Synthetic route

2-(dodecyloxy)tetrahydro-2H-pyran
63588-79-4

2-(dodecyloxy)tetrahydro-2H-pyran

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In methanol at 20℃; for 3.5h; Reagent/catalyst;100%
With tris-(4-bromophenyl)aminium hexachloroantimonate In methanol at 20℃; for 2h;99%
bis(trimethylsilyl)sulphate In methanol; 1,2-dichloro-ethane for 1.5h; Ambient temperature;98%
Dodecanol triethylsilyl ether
145800-64-2

Dodecanol triethylsilyl ether

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With 7,7',8,8'-tetracyanoquinodimethane In water; acetonitrile for 5h; Ambient temperature;100%
With MCM-41 In methanol for 2h; Ambient temperature;99%
With mesoporous silica MCM-41 In methanol at 20℃; for 2h;99%
tert-butyldimethylsilyl ether of dodecan-1-ol
114058-22-9

tert-butyldimethylsilyl ether of dodecan-1-ol

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With polymer-supported dicyanoketene acetal; water In acetonitrile at 20℃; for 24h; Hydrolysis;100%
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In methanol at 20℃; for 1h; Reagent/catalyst;100%
With high p-toluenesulfonate content diphenylamine and terephthalaldehyde resin In methanol at 20℃; for 1h; Reagent/catalyst;100%
1-dodecanyl formate
28303-42-6

1-dodecanyl formate

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With hydrogenchloride In acetone at 20℃; for 0.25h;100%
dodecyl trimethylsilyl ether
6221-88-1

dodecyl trimethylsilyl ether

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With MCM-41 In methanol for 2h; Ambient temperature;100%
With mesoporous silica MCM-41 In methanol at 20℃; for 2h;100%
With polymer-supported dicyanoketene acetal; water In acetonitrile at 20℃; for 1h; Hydrolysis;98%
dodec-2-yn-1-ol
69064-46-6

dodec-2-yn-1-ol

A

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

B

(Z)-dodec-2-en-1-ol
69064-36-4

(Z)-dodec-2-en-1-ol

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;A n/a
B 100%
bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-thiocarbamic acid O-dodecyl ester
910660-86-5

bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-thiocarbamic acid O-dodecyl ester

A

N,N-bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-hydroxylamine

N,N-bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-hydroxylamine

B

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 1h;A n/a
B 100%
dodecyl 2-((2-methoxyphenyl)ethynyl)benzoate

dodecyl 2-((2-methoxyphenyl)ethynyl)benzoate

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In ethanol; benzene at 20℃; for 1h;100%
methyl n-dodecanoate
111-82-0

methyl n-dodecanoate

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With C32H36ClNO2P2Ru; potassium tert-butylate; hydrogen In neat (no solvent) at 120℃; under 38002.6 Torr; for 20h; Autoclave; Green chemistry;99%
With hydrogen In hexane at 200℃; under 15001.5 Torr; for 8h; Reagent/catalyst;99.8%
Stage #1: methyl n-dodecanoate With phenylsilane; fac-[Mn-(xantphos)(CO)3Br] at 120℃; for 12h; Inert atmosphere;
Stage #2: With water; sodium hydroxide In methanol at 20℃; Inert atmosphere;
97%
ethyl laurate
106-33-2

ethyl laurate

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere;99.5%
With potassium borohydride; hafnium tetrachloride In tetrahydrofuran at 40℃; for 9.6h; Inert atmosphere; Cooling with ice;95%
With ethandithiol; sodium tetrahydroborate In tetrahydrofuran for 24h; Heating;94%
Dodecanal
112-54-9

Dodecanal

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With aluminium trichloride; diphenylstibane In tetrahydrofuran for 3h; Ambient temperature;99%
Stage #1: Dodecanal With phenylsilane; potassium tert-butylate In toluene at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With water; sodium hydroxide In toluene at 0 - 20℃;
99%
With LaNi5 hydride In tetrahydrofuran; methanol 1) 0 deg C, 4 h, 2) r.t., 14 h;98%
1-(vinyloxy)dodecane
765-14-0

1-(vinyloxy)dodecane

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With water; dichloro bis(acetonitrile) palladium(II) at 40℃; for 1h;99%
With water; dichloro bis(acetonitrile) palladium(II) In tetrahydrofuran at 40℃; for 1h;98%
dodecyl allyl carbonate
16308-67-1

dodecyl allyl carbonate

2-propanethiol
75-33-2

2-propanethiol

A

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

B

allylisopropyl sulfide
50996-72-0

allylisopropyl sulfide

C

carbon dioxide
124-38-9

carbon dioxide

Conditions
ConditionsYield
With Roussin's red salt ester; tetrabutylammomium bromide; potassium hydride In tetrahydrofuran; ethanol at 40℃;A 99%
B n/a
C n/a
1-dodecene
112-41-4

1-dodecene

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
Stage #1: 1-dodecene With PyBH2I In dichloromethane at 20℃;
Stage #2: With sodium hydroxide; dihydrogen peroxide In methanol; dichloromethane at 0 - 20℃;
98%
Stage #1: 1-dodecene With sodium tetrahydroborate; ethyl iodide In 1,2-dimethoxyethane at 25℃; for 20h;
Stage #2: With dihydrogen peroxide; sodium hydroxide In water at 0 - 25℃; for 0.333333h; Solvent; Reagent/catalyst;
96%
Stage #1: 1-dodecene With borane-THF In tetrahydrofuran; water at 0 - 20℃; for 7h; Inert atmosphere;
Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 6.5h; Inert atmosphere;
95%
Acetic acid dodecyloxymethyl ester
92403-99-1

Acetic acid dodecyloxymethyl ester

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With potassium carbonate In methanol; water98%
C33H44O3

C33H44O3

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In methanol for 0.41h;98%
N-Dodecyloxy-selenobenzimidic acid phenyl ester
195874-65-8

N-Dodecyloxy-selenobenzimidic acid phenyl ester

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 2h; Heating;97%
dodecyl triisopropylsilyl ether

dodecyl triisopropylsilyl ether

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With 2,5-bis(perfluorobutyl)-1,4-benzoquinone In water; acetonitrile at 50℃; for 6h; Reagent/catalyst;97%
With low-loading and alkylated polystyrene-supported-SO3H In water at 100℃; for 12h;94%
tridodecanoylglycerol
538-24-9

tridodecanoylglycerol

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With C24H38Cl2N3PRu; hydrogen; sodium methylate In isopropyl alcohol at 100℃; under 38002.6 Torr; for 2h; Autoclave;97%
With 5 wt% Re/TiO2; hydrogen In neat (no solvent) at 230℃; under 37503.8 Torr; for 30h; Autoclave;81%
lauric acid
143-07-7

lauric acid

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With potassium borohydride; hafnium tetrachloride In tetrahydrofuran at 40℃; for 15.3h; Inert atmosphere; Cooling with ice;96%
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In chloroform at 60℃; for 1h; Inert atmosphere;95%
With 1,1,3,3-Tetramethyldisiloxane; copper(II) bis(trifluoromethanesulfonate) In toluene at 80℃; for 16h; sealed tube;95%
dodecyl methoxymethyl ether
34458-41-8

dodecyl methoxymethyl ether

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With low-loading and alkylated polystyrene-supported-SO3H In water at 100℃; for 24h;96%
With dimethylboron bromide; triethylamine 1) CH2Cl2, 1,2-dichloroethane, -78 deg C, 1h, 2) RT, 1h; Yield given. Multistep reaction;
dodecyl tert-butyldiphenylsilyl ether

dodecyl tert-butyldiphenylsilyl ether

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With low-loading and alkylated polystyrene-supported-SO3H In water at 100℃; for 24h;96%
With acetyl chloride In methanol at 20℃; for 4h;95%
With tetra-N-butylammonium tribromide In methanol; dichloromethane for 6h; Heating;94%
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane for 5h;88%
With 2,5-bis(perfluorohexyl)-3,6-dichloro-1,4-benzoquinone In water; acetonitrile at 50℃; for 6h;84%
dodecyl 4-methylbenzenesulphonate
10157-76-3

dodecyl 4-methylbenzenesulphonate

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 6h; Electrolysis; Green chemistry;96%
1-Methylsulfanylmethoxy-dodecane
87770-95-4

1-Methylsulfanylmethoxy-dodecane

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane 1.) -78 deg C, 1 h 2.) warming up to 0 deg C, 1 h;95%
With dimethylboron bromide; triethylamine 1) CH2Cl2, 1,2-dichloroethane, -78 deg C, 1h, 2) 0 deg C, 1h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: 1) Me2BBr, 2) Et3N / 1) CH2Cl2, 1,2-dichloroethane, -78 deg C, 1h, 2) RT, 1h
2: 1) Me2BBr, 2) Et3N / 1) CH2Cl2, 1,2-dichloroethane, -78 deg C, 1h, 2) RT, 1h
View Scheme
1-Iodododecane
4292-19-7

1-Iodododecane

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide; water at 100℃; for 2.5h;94%
1-dodecylbromide
143-15-7

1-dodecylbromide

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide; water at 100℃; for 5.5h;94%
With oxygen; triethylamine; sodium iodide In acetonitrile at 32℃; for 24h; Schlenk technique; UV-irradiation;50%
1-((dodecyloxy)methyl)-4-methoxybenzene
121505-91-7

1-((dodecyloxy)methyl)-4-methoxybenzene

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; sodium cyanoborohydride In tetrahydrofuran for 10h; Heating;94%
With t-butyl bromide In acetonitrile for 1h; Solvent; Temperature; Reflux; chemoselective reaction;92%
With N,N,N,N-tetraethylammonium tetrafluoroborate In methanol Electrochemical reaction;90%
N,N-diethyldodecanamide
3352-87-2

N,N-diethyldodecanamide

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With n-butyllithium; ammonia borane In tetrahydrofuran; hexane at 23℃; for 1.3h;94%
((dodecyloxy)methyl)benzene
39695-18-6

((dodecyloxy)methyl)benzene

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
With Ti-HMS; hydrogen; 5% Pd on active carbon In methanol under 760 Torr; for 6h; Ambient temperature;94%
Stage #1: ((dodecyloxy)methyl)benzene With Bromotrichloromethane; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In dichloromethane at 20℃; for 12h; Inert atmosphere; Irradiation;
Stage #2: With methanol In dichloromethane Inert atmosphere;
66%
formic acid
64-18-6

formic acid

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

1-dodecanyl formate
28303-42-6

1-dodecanyl formate

Conditions
ConditionsYield
toluene-4-sulfonic acid at 85℃; for 4h; Esterification;100%
With 2-methyl-1-butylimidazolium trifluoroacetate In neat (no solvent) at 70℃; for 1h;96%
Stage #1: formic acid With acetic anhydride at 40℃; for 2h;
Stage #2: 1-dodecyl alcohol at 0 - 20℃; for 15.25h;
94%
With hydrogenchloride
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

lauric acid
143-07-7

lauric acid

Conditions
ConditionsYield
With air; sodium nitrite In trifluoroacetic acid at 0 - 20℃; for 5h;100%
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 12h;100%
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 20℃; for 12h; Reagent/catalyst; Schlenk technique;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Dodecanal
112-54-9

Dodecanal

Conditions
ConditionsYield
With 2,6-dimethylpyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical at 20℃; for 0.5h; electrolysis;100%
Stage #1: 1-dodecyl alcohol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.25h; Oxidation;
Stage #2: With triethylamine at -78 - 20℃; for 0.166667h;
100%
With iodosylbenzene; Cl-CH2-PS supported 5-amino-1,10-phenanthroline-Ru In acetonitrile at 60℃; for 6h;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

dodecyl mesylate
51323-71-8

dodecyl mesylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 0.25h;100%
With triethylamine In dichloromethane at 0℃; for 3h; Inert atmosphere;99%
With triethylamine In dichloromethane at 0℃; for 12h;93%
L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

N-tert-butoxycarbonyl-L-alanine dodecyl ester
124212-36-8

N-tert-butoxycarbonyl-L-alanine dodecyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;100%
papain on XAD-7 In dichloromethane at 37℃; for 18h;55%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

3-tert-butoxycarbonyl-2-chloro-1,3,2-oxazaphospholidine
148160-26-3

3-tert-butoxycarbonyl-2-chloro-1,3,2-oxazaphospholidine

3-tert-butoxycarbonyl-2-dodecyloxy-1,3,2-oxazaphospholidine
148160-28-5

3-tert-butoxycarbonyl-2-dodecyloxy-1,3,2-oxazaphospholidine

Conditions
ConditionsYield
With triethylamine In dichloromethane -60 deg C to r.t., 1 h;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

2-chloro-3-methyl-1,3,2-oxazaphospholidine
22082-71-9

2-chloro-3-methyl-1,3,2-oxazaphospholidine

2-Dodecyloxy-3-methyl-1,3,2-oxazaphosphacyclopentane
129274-35-7

2-Dodecyloxy-3-methyl-1,3,2-oxazaphosphacyclopentane

Conditions
ConditionsYield
With triethylamine In dichloromethane for 1h; -30 - -40 deg C to RT;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

3-tert-2-chloro-1,3,2-oxazaphosphacyclopentane
67105-49-1

3-tert-2-chloro-1,3,2-oxazaphosphacyclopentane

3-tert-butyl-2-dodecyloxy-1,3,2-oxazaphosphacyclopentane
139715-61-0

3-tert-butyl-2-dodecyloxy-1,3,2-oxazaphosphacyclopentane

Conditions
ConditionsYield
With triethylamine In dichloromethane for 1h; -60 deg C to rt;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

formic acid ethyl ester
109-94-4

formic acid ethyl ester

1-dodecanyl formate
28303-42-6

1-dodecanyl formate

Conditions
ConditionsYield
cerium (IV) sulfate; silica gel for 1h; Heating;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

n-dodecyl chloroformate
24460-74-0

n-dodecyl chloroformate

Conditions
ConditionsYield
With pyridine In tetrachloromethane at -15 - 20℃;100%
With pyridine In tetrahydrofuran for 2h;
With pyridine In chloroform for 2h; ice cooling;
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

bromoacetic acid
79-08-3

bromoacetic acid

dodecyl bromoacetate
3674-07-5

dodecyl bromoacetate

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol; toluene-4-sulfonic acid In toluene for 7h; Reflux;100%
With toluene-4-sulfonic acid; 1-octyl-3-methylimidazolium tetrafluoroborate at 80℃; for 1h;98%
With toluene-4-sulfonic acid In 5,5-dimethyl-1,3-cyclohexadiene95%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

perbenzyl fucosyl bromide
33639-77-9

perbenzyl fucosyl bromide

(3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-dodecyloxy-6-methyl-tetrahydro-pyran

(3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-dodecyloxy-6-methyl-tetrahydro-pyran

Conditions
ConditionsYield
With 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine for 4h; Substitution;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

(2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-iodo-6-methyl-tetrahydro-pyran
250691-61-3

(2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-iodo-6-methyl-tetrahydro-pyran

(3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-dodecyloxy-6-methyl-tetrahydro-pyran

(3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-dodecyloxy-6-methyl-tetrahydro-pyran

Conditions
ConditionsYield
With 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine for 4h; Substitution;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

3-(thymine-1-yl)propionic acid
6214-59-1

3-(thymine-1-yl)propionic acid

dodecyl 3-(thymin-1-yl)propionate

dodecyl 3-(thymin-1-yl)propionate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In pyridine at 0 - 20℃; for 48h;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

4-(4-bromophenyl)-4-oxo-butyric acid
6340-79-0

4-(4-bromophenyl)-4-oxo-butyric acid

dodecyl 4-(4-bromophenyl)-4-oxobutanoate
375826-30-5

dodecyl 4-(4-bromophenyl)-4-oxobutanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;99%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

N-t-butoxycarbonyl-N-methyl-β-alanine
124072-61-3

N-t-butoxycarbonyl-N-methyl-β-alanine

Boc-MeβAla-O-n-dodecyl
654651-62-4

Boc-MeβAla-O-n-dodecyl

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

dodecyl hexadecanoic acid ester
42232-29-1

dodecyl hexadecanoic acid ester

Conditions
ConditionsYield
With zirconium(IV) oxychloride In 1,3,5-trimethyl-benzene at 162℃; for 24h;100%
With toluene-4-sulfonic acid In benzene for 30h; Reflux;100%
iron(III) chloride In 1,3,5-trimethyl-benzene at 162℃; for 24h;99%
C15H12ClF18NS
910660-81-0

C15H12ClF18NS

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

bis-(4,4,5,5,6,6,7,7,7-nonafluoro-heptyl)-thiocarbamic acid O-dodecyl ester
910660-85-4

bis-(4,4,5,5,6,6,7,7,7-nonafluoro-heptyl)-thiocarbamic acid O-dodecyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 12h;100%
C19H12ClF26NS
910660-82-1

C19H12ClF26NS

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-thiocarbamic acid O-dodecyl ester
910660-86-5

bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-thiocarbamic acid O-dodecyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 12h;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

3-(tert-butyldimethylsilyloxy)glutaric anhydride
91424-40-7

3-(tert-butyldimethylsilyloxy)glutaric anhydride

3-(tert-butyldimethylsilyloxy)-5-oxo-5-(dodecyloxy)pentanoic acid
916441-89-9

3-(tert-butyldimethylsilyloxy)-5-oxo-5-(dodecyloxy)pentanoic acid

Conditions
ConditionsYield
In toluene Heating;100%
In toluene for 24h; Reflux;95%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Pyroglutamic acid
149-87-1

Pyroglutamic acid

ethyl 2-oxopyrrolidine-5-carboxylate
66183-71-9

ethyl 2-oxopyrrolidine-5-carboxylate

2-pyrrolidone-5-carboxylic acid n-dodecyl ester
75444-31-4

2-pyrrolidone-5-carboxylic acid n-dodecyl ester

Conditions
ConditionsYield
Novozym 435 at 60℃; under 15.0015 Torr; for 24h; Enzymatic reaction;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

C29H38O6
1170721-83-1

C29H38O6

C41H62O6

C41H62O6

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;100%

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112-53-8Relevant articles and documents

Kinetics of the Acid-catalysed Hydrolysis of Dodecylsulphate and Dodecyldiethoxysulphate Surfactants in Concentrated Micellar Solutions. Part 1. - Effects of Acid and Surfactant Concentrations and of the Nature and Concentration of Counterions

Garnett, Christopher J.,Lambie, Alan J.,Beck, William H.,Liler, Milica

, p. 953 - 964 (1983)

The rates of the acid-catalysed hydrolysis of sodium dodecylsulphate (SDS) and sodium dodecyldiethoxysulphate (SDE2S) have been investigated in concentrated surfactant solutions (0.035 - 0.6 mol dm-3).The acid concentration dependence of the initial rates shows a 'saturation' effect, whereas increasing surfactant concentrations above the c.m.c. lead to a maximum in the k2,obs values, beyond which they decrease sharply.These results are discussed in terms of the ion-exchange pseudophase model of the miceller reaction.The nature of the counterion has an effect on k2,obs, the values following the sequence NH4 > Li > Na >> Mg.This has been ascribed to differences in the ion-exchange constants, KH/X, of these cations in the Stern layer of the micelles with the hydrogen ion.Maintaining the total counterion concentration and the ratio of concentrations of surfactant counterion to the concentration of hydrogen ion constant (at 30, i.e. 0.6 : 0.02 mol dm-3) largely eliminates the decrease in the k2,obs values with increasing surfactant concentration, as expected from the pseudo-phase ion-exchange model.Quantitative agreement between theory and experiment is less good, however, owing at least partly to deviations from ideality in solutions of high ionic strength.

Acid-catalyzed hydrolysis of sodium dodecyl sulfate

Nakagaki,Yokoyama

, p. 1047 - 1052 (1985)

The acid-catalyzed hydrolysis of sodium dodecyl sulfate (1) and the effect of 1-dodecanol (2) on this hydrolysis were investigated. The rate of hydrolysis was followed by measuring the rate of production of HSO4- using a pH-stat. The rate constant (κ(H+)) below the critical micelle concentration (CMC) increased with increasing concentrations of 2, up to a mole ratio of 0.5 for 2 to 1, after which the hydrolysis rate was independent of the concentration of 2. These results suggest the possible formation of a complex between 1 and 2. A micellar solution of pure sodium dodecyl sulfate (20 mM) hydrolyzed 50 times faster than that of a premicellar solution at the same pH. Plots of log κ versus pH were linear with a slope of -1 at pH 4.3. At a constant pH, the addition of NaCl resulted in a decrease in the rate of hydrolysis of a micellar solution. This is probably due to the reduction of concentration of protons at the micelle surface. Furthermore, κ(H+) was also decreased by the addition of 2 in the region where 2 is solubilized in the micelle; again, this was probably due to the reduction of the charge density (σ) on the surface of the micelle.

An effective hydrolysis of crowded chiral esters

Vávra, Jan,Streinz, Ludvík,Vodi?ka, Petr,Budě?ínsky, Milo?,Koutek, Bohumír

, p. 1886 - 1888 (2002)

Trifluoromethanesulfonic acid-coated silica in the absence of solvents is an effective reagent for hydrolysis of sterically crowded chiral esters giving chiral acids in good chemical and optical yield. On the other hand, the method was unsuitable for the

Cleavage of protecting groups catalysed by π-acceptors

Tanemura, Kiyoshi,Nishida, Yoko,Suzuki, Tsuneo,Satsumabayashi, Koko,Horaguchi, Takaaki

, p. 40 - 41 (1999)

The cleavage of protecting groups is caused by the acidic adducts produced from the methanolysis of acceptors.

Selective conversion of coconut oil to fatty alcohols in methanol over a hydrothermally prepared Cu/SiO2 catalyst without extraneous hydrogen

Wu, Liubi,Li, Lulu,Li, Bolong,Zhao, Chen

, p. 6152 - 6155 (2017)

A novel one-pot approach selects a hydrothermally synthesized Cu/SiO2 catalyst (consisting of Cu2O·SiO2 and Cu0 surface species) to catalyze the reduction of a series of fatty esters, fatty acids, and coconut oil to fatty alcohols at 240 °C in methanol without extraneous hydrogen, attaining around 85% conversion and 100% selectivity.

A glucose-activatable trimodal glucometer self-assembled from glucose oxidase and MnO2 nanosheets for diabetes monitoring

Chen, Jin-Long,Li, Li,Wang, Shuo,Sun, Xiao-Yan,Xiao, Lu,Ren, Jia-Shu,Di, Bin,Gu, Ning

, p. 5336 - 5344 (2017)

Daily monitoring of blood glucose is of great importance for the treatment of diabetes mellitus. Herein, we present an ensemble glucometer with a sandwich structure formed by the spontaneous entrapment of glucose oxidase (GOD) onto manganese dioxide nanosheets (MnO2 NSs) via the hydrophobic effect and hydrogen bond interaction. Within the hybrid glucometer, the ultrathin MnO2 NSs act as an enzyme nanosupport and target-activated signal transducer. Trimodal self-indication by fluorescence (FL) and UV-absorbance (UV) and magnetic resonance signal (MRS) activation with glucose-specificity provides multiple response signals to glucose. Taking account of its operational simplicity and convenience, even being observable by the naked eye, a detection limit as low as 0.1 ;M was obtained by using the ensemble glucometer in a colorimetric assay, whilst the precision for 11 replicated detections of 10 M glucose was 3.5% (relative standard deviation, RSD). Notably, the value of the Michaelis-Menton constant of GOD involved the presented glucometer is estimated to be 0.051 mM, showing an exceptional enhanced enzymatic activity of free GOD measured by far. The designed glucometer, with its high sensitivity and simplicity highlighted, was capable of routine blood glucose monitoring for type-I diabetes mellitus in rats. Furthermore, the fully integrated platform can be readily generalized in principle for a number of biomarkers for point of care diagnostics in the future.

Benzimidazoline-dimethoxypyrene. An effective promoter system for photoinduced electron transfer promoted reductive transformations of organic compounds

Hasegawa, Eietsu,Hirose, Harumi,Sasaki, Kosuke,Takizawa, Shinya,Seida, Takayuki,Chiba, Naoki

, p. 1147 - 1161 (2009)

2-(p-Methoxyphenyl)-1,3-dimethylbenzimidazoline (ADMBI) and 2-(o-hydroxyphenyl)-1,3-dimethylbenzimidazoline (HPDMBI) are used as reducing reagents in 1,8-dimethoxypyrene (1,8-DMP) sensitized, photoinduced electron transfer (PET) reactions. This system was effectively used for PET induced, reductive transformations of various organic substrates, including α,β-epoxy ketones, the olefin tethered 2-bromomethyl-l-tetralone, and o-allyloxy-iodobenzene, as well as for the deprotection reactions of dodecyl-2-benzoylbenzoate and N-sulfonylindole. The results of studies show that 1,8-DMP is a more effective sensitizer than the previously used 9-methylcarbazole for deprotection of N-methyl-4-picolinium ester.

Transformation of methyl laurate into lauryl alcohol over a Ru-Sn-Mo/C catalyst by using zerovalent iron and water as an in situ hydrogen source

Sagata, Kunimasa,Hirose, Mina,Hirano, Yoshiaki,Kita, Yuichi

, p. 85 - 91 (2016)

Hydrogenation and hydrogenolysis reactions, which are used in the chemical industry for the synthesis of organic compounds, are very expensive operations because of the need for facilities that can liquefy, transport, and store the hydrogen produced through steam reforming of natural gas. We have therefore developed a novel approach for hydrogenation that does not require the use of high-cost facilities. Using this, zerovalent iron (Fe) and water (H2O) are introduced as an in situ hydrogen donor system for the transformation of methyl laurate into lauryl alcohol over a Ru-based catalyst. This combination of a Ru-Sn-Mo/C catalyst with a Fe/H2O system showed significantly higher transformation rates for the conversion of methyl laurate into lauryl alcohol than a conventional reaction system that uses pressurized hydrogen. The reason for this is that the new system produces lauric acid as an intermediate during the reaction, which is more efficiently hydrogenized into lauryl alcohol over the Ru-Sn-Mo/C catalyst. The Fe/H2O system played two important roles: a hydrogen source for the hydrogenation reaction and a catalyst for the generation of lauric acid by methyl laurate hydrolysis.

Riemschneider,R.,Hoyer,G.-A.

, p. 642 - 651 (1968)

Influence of Higher Alcohols on Acid-Catalyzed Hydrolysis of Sodium Dodecyl Sulfate. Effect of Complex Formation

Nakagaki, Masayuki,Yokoyama, Shoko

, p. 935 - 936 (1986)

The order of effectiveness of 1-alkanols for increasing the rate of acid-catalyzed hydrolysis of sodium dodecyl sulfate is 1-dodecanol>-tetradecanol>>1-decanol.The effect of 1-alkanols on this hydrolysis is discussed from the viewpoint of formation of complexes composed of SDS and 1-alkanol.

Preparation of cyclohexene-d10 by H/D-exchange reaction

Ishibashi, Kenichi,Matsubara, Seijiro

, p. 724 - 725 (2007)

Preparation of fully deuterium-labeled cyclohexene by H/D-exchange reaction was performed efficiently in the presence of ruthenium catalyst under irradiation of microwaves. The reaction proceeds via a repetition of hydroruthenation and β-elimination. Copyright

Adkins,Burgoyne,Schneider

, p. 2626 (1950)

Lithium amidotrihydroborate, a powerful new reductant. Transformation of tertiary amides to primary alcohols

Myers, Andrew G.,Yang, Bryant H.,Kopecky, David J.

, p. 3623 - 3626 (1996)

Lithium amidotrihydroborate (LiH2NBH3, LAB) is a new and highly nucleophilic reducing agent that is easily prepared by deprotonation of the commercial reagent borane-ammonia complex (H2NBH3) with n-BuLi in tetrahydrofuran (THF) at 0°C. LAB is found to be a superior reagent for the transformation of tertiary amides into the corresponding primary alcohols.

Elucidation of the mechanism of titanocene-mediated epoxide opening by a combined experimental and theoretical approach

Daasbjerg, Kim,Svith, Heidi,Grimme, Stefan,Gerenkamp, Mareike,Mueck-Lichtenfeld, Christian,Gansaeuer, Andreas,Barchuk, Andriy,Keller, Florian

, p. 2041 - 2044 (2006)

(Figure Presented) Steric effects govern the catalytic reductive epoxide ring opening. This is the result of combined experimental and theoretical studies, which revealed interesting features of the catalyst structure, substrate binding, transition state (see picture), and reaction energies. In light of these, highly selective conditions for the ring opening can be proposed.

Deactivation mechanism of Cu/Zn catalyst poisoned by organic chlorides in hydrogenation of fatty methyl ester to fatty alcohol

Huang, Hui,Wang, Shaohong,Wang, Shujia,Cao, Guiping

, p. 351 - 357 (2010)

The mechanism of deactivation of Cu/Zn catalyst poisoned by organic chlorides in hydrogenation of methyl laurate to lauryl alcohol in a slurry phase was studied in a stirred autoclave. The catalystwas prepared by co-precipitation, and the un-poisoned and poisoned catalysts were characterized using XRD, BET, ICP-AES and SEM, respectively. The results indicated that both of catalytic activity and selectivity decreased with increasing amount of chlorides in methyl laurate. According to the characterization of the catalysts, the main causes for the chlorine deactivation of the Cu/Zn catalyst were that the chlorides could modify the valence state of active sites, decrease the BETsurface area, and promote the growth of crystal and catalyst agglomeration. Further investigation indicated that chlorine atom decomposed from the chlorides combined with ZnO to produce ZnCl2, which could be dissolved in the liquid and promote ester-exchange reaction to lauryl laurate as Lewis acid.

Hydrodeoxygenation of non-edible bio-lipids to renewable hydrocarbons over mesoporous SiO2-TiO2 supported NiMo bimetallic catalyst

Ba, Wenxia,Fu, Lin,Li, Xin,Li, Yongfei,Liu, Yuejin,Zhang, Simiao,Zhao, Jingxuan

, (2022/02/17)

Ni-catalysts are promising candidate for fatty acid hydrodeoxygenation (HDO), but are limited by their quite poor HDO selectivity. Herein, a mesoporous Ni-Mo/SiO2-TiO2 catalyst was prepared by precipitation and impregnation method and used for methyl laurate HDO, yielding 96.3% n-dodecane yield at full methyl laurate conversion. Non-edible bio-lipids such as jatropha oil and waste cooking oil also converted to n-C14+16+18 hydrocarbons with yields of 94.3% and 92.4%, respectively. Besides, Ni-Mo/SiO2-TiO2 shows strong chemoselectivity towards the HDO of ester groups. Experimental results showed that Mo-addition and Ti/Si molar ratio strongly influenced HDO selectivity. Oxygen vacancies formed on partial reduced TiO2 surface securely bond Ni NPs and activate C[dbnd]O/C–O bonds, improving Ni NPs dispersion and promoting R–COOCH3→R–CHO reduction. Additional, Mo-addition switches reactant adsorption configuration from η1(C)-acyl to η2(C,O)-aldehyde, promoting the formation of R–CH2OH intermediate. Moreover, abundant Br?nsted acidic sites (Mo4+–OH, Mo6+–OH, hydroxy groups) facilitate the HDO of R-CH2OH to R-CH3.

Defunctionalization of sp3 C–Heteroatom and sp3 C–C Bonds Enabled by Photoexcited Triplet Ketone Catalysts

An, Juzeng,Gu, Yiting,Martin, Ruben,Wakeling, Matthew,Yin, Hongfei

, p. 1031 - 1036 (2022/01/19)

A general strategy for enabling a light-induced defunctionalization of sp3 C–heteroatom and sp3 C–C bonds with triplet ketone catalysts and bipyridine additives is disclosed. This protocol is characterized by its broad scope without recourse to transition metal catalysts or stoichiometric exogeneous reductants, thus offering a complementary technique for activating σ sp3 C–C(heteroatom) bonds. Preliminary mechanistic studies suggest that the presence of 2,2′-bipyridines improves the lifetime of ketyl radical intermediates.

Discovery of Anti-TNBC Agents Targeting PTP1B: Total Synthesis, Structure-Activity Relationship, in Vitro and in Vivo Investigations of Jamunones

Hu, Caijuan,Li, Guoxun,Mu, Yu,Wu, Wenxi,Cao, Bixuan,Wang, Zixuan,Yu, Hainan,Guan, Peipei,Han, Li,Li, Liya,Huang, Xueshi

supporting information, p. 6008 - 6020 (2021/05/06)

Twenty-three natural jamunone analogues along with a series of jamunone-based derivatives were synthesized and evaluated for their inhibitory effects against breast cancer (BC) MDA-MB-231 and MCF-7 cells. The preliminary structure-activity relationship revealed that the length of aliphatic side chain and free phenolic hydroxyl group at the scaffold played a vital role in anti-BC activities and the methyl group on chromanone affected the selectivity of molecules against MDA-MB-231 and MCF-7 cells. Among them, jamunone M (JM) was screened as the most effective anti-triple-negative breast cancer (anti-TNBC) candidate with a high selectivity against BC cells over normal human cells. Mechanistic investigations indicated that JM could induce mitochondria-mediated apoptosis and cause G0/G1 phase arrest in BC cells. Furthermore, JM significantly restrained tumor growth in MDA-MB-231 xenograft mice without apparent toxicity. Interestingly, JM could downregulate phosphatidylinositide 3-kinase (PI3K)/Akt pathway by suppressing protein-tyrosine phosphatase 1B (PTP1B) expression. These findings revealed the potential of JM as an appealing therapeutic drug candidate for TNBC.

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