25354-97-6

Basic information

• Product Name: 2-HEXYLDECANOIC ACID
• Synonyms: c16guerbetfattyacid;Decanoicacid,2-hexyl-;JARICTM I-16;JARIC I-16;ISOPALMIC ACID;ISOPALMITIC ACID;2-N-HEXYLDECANOIC ACID;2-HEXYLDECANOIC ACID
• CAS NO: 25354-97-6
• Molecular Formula: C₁₆H₃₂O₂
• Molecular Weight: 256.42
• EINECS: 246-885-9
• Product Categories: C13 to C42+;Carbonyl Compounds;Carboxylic Acids
• Mol File: 25354-97-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 10°C
• Boiling Point: 165-168°C 2mm
• Flash Point: 174°C
• Appearance: colourless to yellow liquid
• Density: 0,88 g/cm3
• Vapor Pressure: 1.6E-06mmHg at 25°C
• Refractive Index: 1.4460
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.90±0.40(Predicted)
• Water Solubility: 70.83μg/L at 20℃
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,4709
• BRN: 1777217
• CAS DataBase Reference: 2-HEXYLDECANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HEXYLDECANOIC ACID(25354-97-6)
• EPA Substance Registry System: 2-HEXYLDECANOIC ACID(25354-97-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 1
• RTECS: HD9750000
• TSCA: Yes
• Hazardous Substances Data: 25354-97-6(Hazardous Substances Data)

Usage

Chemical Properties

colourless to yellow liquid

Uses

Different sources of media describe the Uses of 25354-97-6 differently. You can refer to the following data:
1. 2-Hexyldecanoic Acid is used in preparation of cationic lipid; pharmaceutical compound and treatment agent containing lipid and siRNA for suppressing expression of hepatitis B virus gene.
2. 2-Hexyldecanoic acid may be used as amidating agent for the suppression of side-chain crystallization during the synthesis of amphiphilic macromolecules. It may be employed as a surrogate carboxylic acid in a study.

General Description

2-Hexyldecanoic acid is a carboxylic acid having branched carbon chains.

InChI:InChI=1/C16H32O2/c1-3-5-7-9-10-12-14-15(16(17)18)13-11-8-6-4-2/h15H,3-14H2,1-2H3,(H,17,18)

Synthetic route

2-hexyl-2-octylmalonic acid (87549-17-5) → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
at 160℃; Inert atmosphere;	96.31%
With glass powder at 145℃; for 3.5h;	95%

methanol (67-56-1) + 1-Chlorohexane (544-10-5) + methyl octanate (111-11-5) → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
Stage #1: methanol; 1-Chlorohexane; methyl octanate With sodium hydroxide at 20 - 60℃; for 6h; Large scale; Stage #2: With water; sodium hydroxide at 60℃; for 6h; Large scale;	91.3%

1-decanoic acid (334-48-5) + 1-Iodohexane (638-45-9) → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
Stage #1: 1-decanoic acid With sodium hydride; lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: 1-Iodohexane at 45℃; for 6h;	65%

oct-1-ene (111-66-0) + Octanoic acid (124-07-2) → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
With di-tert-butyl peroxide at 150 - 155℃;

2-hexyl-dec-2ξ-enoic acid → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
With ethanol; platinum Hydrogenation;

n-hexyl-n-octyl-malonic acid → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
Erhitzen ueber den Schmelzpunkt;

diethyl 2-hexylmalonate (5398-10-7) → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80.6 percent / Na / ethanol 2: 88.4 percent / KOH / H2O / 5 h / 90 °C 3: 95 percent / glass powder / 3.5 h / 145 °C View Scheme

1-bromo-hexane (111-25-1) + (+-)-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-benzochromene-1,3-diol → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 82 percent / Na / ethanol / 2.5 h / Heating 2: 80.6 percent / Na / ethanol 3: 88.4 percent / KOH / H2O / 5 h / 90 °C 4: 95 percent / glass powder / 3.5 h / 145 °C View Scheme

diethyl 2-hexyl-2-octylmalonate (87549-16-4) → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88.4 percent / KOH / H2O / 5 h / 90 °C 2: 95 percent / glass powder / 3.5 h / 145 °C View Scheme

2-hexyldecan-1-ol (2425-77-6) + sulfuric acid (7664-93-9) → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
With potassium permanganate In dichloromethane

1-bromo-octane (111-83-1) → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium methylate / ethanol / 3 h / Reflux; Large scale 1.2: 3 h / Reflux; Large scale 2.1: sodium hydroxide / ethanol; water / 12 h / Reflux 3.1: 160 °C / Inert atmosphere View Scheme

1-bromo-hexane (111-25-1) → 2-hexyldecanoic acid (25354-97-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium methylate / ethanol / 3 h / Reflux; Large scale 1.2: 3 h / Reflux; Large scale 2.1: sodium hydroxide / ethanol; water / 12 h / Reflux 3.1: 160 °C / Inert atmosphere View Scheme

2-hexyldecanoic acid (25354-97-6) → 2-hexyldecanoic acid chloride (74918-57-3)

Conditions	Yield
With thionyl chloride In dichloromethane at 20℃; Inert atmosphere;	100%
With thionyl chloride In dichloromethane for 1h; Reagent/catalyst; Solvent; Reflux;	92.1%
With thionyl chloride In tetrachloromethane for 3.5h; Heating / reflux;	91%

Diethylene glycol monobutyl ether (112-34-5) + 2-hexyldecanoic acid (25354-97-6) → 2-(2-butoxyethoxy)ethyl 2-hexyldecanoate

Conditions	Yield
With p-toluenesulfonic acid monohydrate	99%
With p-toluenesulfonic acid monohydrate	99%

n-heptan1ol (111-70-6) + 2-hexyldecanoic acid (25354-97-6) → heptyl 2-hexyldecanoate

Conditions	Yield
With p-toluenesulfonic acid monohydrate	98%

diazomethane (186581-53-3, 908094-01-9) + 2-hexyldecanoic acid (25354-97-6) → methyl 2-hexyldecanoate (54889-76-8)

Conditions	Yield
In diethyl ether	95%

2-hexyldecanoic acid (25354-97-6) → sodium 2-hexyldecanoate (536-37-8)

Conditions	Yield
With sodium carbonate In ethanol; water for 2h;	90%

2-hexyldecanoic acid (25354-97-6) + tetra(p-hydroxyphenyl)ethylene (119301-59-6) → C90H140O8

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 18h;	87%

2-hexyldecanoic acid (25354-97-6) + isopropyl alcohol (67-63-0) → isopropyl 2-hexyldecanoate (181319-53-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	86%

2-hexyldecanoic acid (25354-97-6) + nonyl alcohol (143-08-8) → nonyl 2-hexyldecanoate

Conditions	Yield
With p-toluenesulfonic acid monohydrate	86%

2-hexyldecanoic acid (25354-97-6) + (2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yI)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-2-ethynyltetrahydrofuran-3-ol → (2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-2-ethynyltetrahydrofuran-3-yl 2-hexyldecanoate

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;	84%

4-hydroxymethyl-1,3-dioxolan-2-one (931-40-8) + 2-hexyldecanoic acid (25354-97-6) → (2-oxo-1,3-dioxolan-4-yl)methyl 2-hexyldecanoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	82%

2-hexyldecanoic acid (25354-97-6) → pentadecane (629-62-9) + carbon monoxide (201230-82-2)

Conditions	Yield
With hydrogen at 200℃; under 7500.75 Torr; for 24h; Microwave irradiation;	A 78% B n/a

2-hexyldecanoic acid (25354-97-6) + 10-ethyl-7-tetradecanol → 2-hexyl decanoic acid 1-hexyl-4-ethyloctyl

Conditions	Yield
With titanium(IV) isopropylate at 200 - 210℃; for 14h; Dean-Stark;	75%

2-hexyldecanoic acid (25354-97-6) → 2-hexyldecanoyl amide (1608483-87-9)

Conditions	Yield
With thionyl chloride; ammonia In water for 0.5h; Reflux;	74%
Multi-step reaction with 2 steps 1: oxalyl dichloride / benzene / 4 h 2: ammonium hydroxide / dichloromethane View Scheme
Multi-step reaction with 2 steps 1: oxalyl dichloride / benzene 2: ammonium hydroxide / dichloromethane; water / 2 h View Scheme

2-hexyldecanoic acid (25354-97-6) + 3-(4-fluoro-phenyl)-propenal (51791-26-5, 24654-55-5) → C24H39FO

Conditions	Yield
With piperazine; 9-(2-chlorophenyl)acridine; tetrakis(acetonitrile)copper(I)tetrafluoroborate In dichloromethane at 25 - 27℃; for 14h; Irradiation;	71%

2-hexyldecanoic acid (25354-97-6) + 2,5-diaminobenzene-1,4-dithiol bis(hydrochloride) → 2,6-bis(1-hexylnonyl)benzo[1,2-d:4,5-d']bisthiazole

Conditions	Yield
Stage #1: 2,5-diaminobenzene-1,4-dithiol bis(hydrochloride) at 100℃; under 7.50075 Torr; for 2h; Inert atmosphere; Stage #2: 2-hexyldecanoic acid With phosphorus pentoxide at 60 - 140℃; for 18h; Inert atmosphere;	70.1%

2-hexyldecanoic acid (25354-97-6) + isobutyl 10,11-dihydroxynonadecanesulfonate → isobutyl 10,11-bis(2-hexyldecanoyloxy)nonadecanesulfonate

Conditions	Yield
Stage #1: 2-hexyldecanoic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Cooling with ice; Inert atmosphere; Stage #2: isobutyl 10,11-dihydroxynonadecanesulfonate With dmap In dichloromethane at 20℃; for 16h; Cooling with ice; Inert atmosphere;	70%

2-hexyldecanoic acid (25354-97-6) + S-(difluoromethyl) benzenesulfonothioate → C16H32F2S

Conditions	Yield
With dipotassium peroxodisulfate; sodium dodecyl-sulfate; silver nitrate In water at 50℃; for 6h; Schlenk technique; Inert atmosphere;	69%

2-hexyldecanoic acid (25354-97-6) + 6,6'-(1-(2-(dimethylamino)ethyl)hydrazine-1,2-diyl)bis(hexan-1-ol) → (1-(2-(dimethylamino)ethyl)hydrazine-1,2-diyl)bis(hexane-6,1-diyl) bis(2-hexyldecanoate)

Conditions	Yield
With dmap; 1,2-dichloro-ethane In dichloromethane	65%

2-hexyldecanoic acid (25354-97-6) → 7-azidopentadecane

Conditions	Yield
With phenylsulfonyl azide; dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 55℃; under 760.051 Torr; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	64%

cyclopent-2-enone (930-30-3) + 2-hexyldecanoic acid (25354-97-6) → C20H38O

Conditions	Yield
With piperazine; 9-(2-chlorophenyl)acridine; tetrakis(acetonitrile)copper(I)tetrafluoroborate In dichloromethane at 25 - 27℃; for 14h; Irradiation;	62%

2-hexyldecanoic acid (25354-97-6) + 2,2-dinitropropanol (918-52-5) → 2,2-dinitropropyl 2-hexyldecanoate

Conditions	Yield
With polyphosphoric acid In 1,2-dichloro-ethane	60%

2,2,2-trifluoroethanol (75-89-8) + 2-hexyldecanoic acid (25354-97-6) → 2,2,2-trifluoroethyl 2-hexyldecanoate

Conditions	Yield
With immobilized Candida antarctica Lipase B In tert-butyl alcohol at 46℃; for 1h; Molecular sieve; Microwave irradiation; Inert atmosphere; Enzymatic reaction;	59%

2-hexyldecanoic acid (25354-97-6) → 7-fluoropentadecane

Conditions	Yield
With caesium carbonate; Selectfluor; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 20℃; for 72h; Inert atmosphere; Schlenk technique; Irradiation;	55%

diethyl ethylidenemalonate (1462-12-0) + 2-hexyldecanoic acid (25354-97-6) → (±)-diethyl 2-(3-hexylundecan-2-yl)malonate

Conditions	Yield
With dipotassium hydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Michael Addition; Inert atmosphere; Photolysis; Sealed tube;	53%

2-hexyldecanoic acid (25354-97-6) + trifluoroacetic anhydride (407-25-0) → 1,1,1-trifluoro-3-hexylundecan-2-one

Conditions	Yield
Stage #1: 2-hexyldecanoic acid; trifluoroacetic anhydride With pyridine In toluene at 100℃; for 48h; Stage #2: With water In toluene at 45℃; for 2h;	41%
Stage #1: 2-hexyldecanoic acid; trifluoroacetic anhydride With pyridine In toluene at 60 - 65℃; for 4h; Inert atmosphere; Stage #2: With water In toluene at 57 - 60℃; for 1h; Inert atmosphere;	41%

2-hexyldecanoic acid (25354-97-6) + C33H68N2O3 → C65H128N2O5

Conditions	Yield
With dicyclohexyl-carbodiimide	38%

2-hexyldecanoic acid (25354-97-6) → pentadecane (629-62-9) + (E)-pentadec-7-ene (16416-37-8) + 9,10-dihexyloctadecane

Conditions	Yield
With potassium methanolate In methanol at 40 - 45℃; electrolysis: anode: platinum foil; current source: galvanostat; current density 200 mA cm-2; current consumption: 1.4 F mol-1; cell voltage 11-15 V;	A 17% B 28% C 34%

Upstream product

• 111-66-0 oct-1-ene 
• 124-07-2 Octanoic acid 
• 111-83-1 1-bromo-octane 
• 111-25-1 1-bromo-hexane 
• 67-56-1 methanol 
• 544-10-5 1-Chlorohexane 
• 111-11-5 methyl octanate 
• 334-48-5 1-decanoic acid 
• 638-45-9 1-Iodohexane 
• 2425-77-6 2-hexyldecan-1-ol 
• 7664-93-9 sulfuric acid 
• 87549-16-4 diethyl 2-hexyl-2-octylmalonate 
• 5398-10-7 diethyl 2-hexylmalonate 
• 87549-17-5 2-hexyl-2-octylmalonic acid 

Downstream Products

• 2425-77-6 2-hexyldecan-1-ol 
• 52997-43-0 7-(bromomethyl)pentadecane 
• 87549-18-6 2-hexyldecyl-4-methylbenzene sulfonate 
• 629-62-9 pentadecane 
• 201230-82-2 carbon monoxide 
• 62281-05-4 2-n-hexyldecan-1-amine 
• 2036272-55-4 1,2-distearoyl-sn-glycero-3-phosphocholine 
• 1442749-92-9 dimethyl 5-(2-butyloctanamido)isophthalic acid 

Relevant articles and documents

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CATIONIC LIPIDS FOR NUCLEIC ACID DELIVERY AND PREPARATION THEREOF

The present invention provides cationic lipids and lipid nanoparticle formulations comprising these lipids, alone or in combination with other lipids. These lipid nanoparticles may be formulated with nucleic acids to facilitate their intracellular delivery both in vitro and for therapeutic applications. The present invention also provides methods of chemical synthesis of these lipids, lipid nanoparticle preparation and formulation with nucleic acids.

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