142-91-6

Basic information

• Product Name: Isopropyl palmitate
• Synonyms: PALMITIC ACID ISOPROPYL ESTER;1-Methylethyl ester1-methylethyl hexandecanoate;1-methylethyl hexadecanoate;1-Methylethylhexadecanoate;2-propyl hexadecanoate;Crodamol IPP;crodamolipp;Deltyl
• CAS NO: 142-91-6
• Molecular Formula: C₁₉H₃₈O₂
• Molecular Weight: 298.5
• EINECS: 205-571-1
• Product Categories: Hair Care;Skin Care;Bioactive Small Molecules;Building Blocks;C12 to C63;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Esters;I;Organic Building Blocks;Cosmetic raw material
• Mol File: 142-91-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 11-13 °C(lit.)
• Boiling Point: 160°C 2mm
• Flash Point: >230 °F
• Appearance: /
• Density: 0.852 g/mL at 25 °C(lit.)
• Vapor Pressure: 8.44E-05mmHg at 25°C
• Refractive Index: n20/D 1.438(lit.)
• Storage Temp.: 2-8°C
• Solubility: <0.001g/l
• Water Solubility: Not miscible or difficult to mix with water.
• BRN: 1786567
• CAS DataBase Reference: Isopropyl palmitate(CAS DataBase Reference)
• NIST Chemistry Reference: Isopropyl palmitate(142-91-6)
• EPA Substance Registry System: Isopropyl palmitate(142-91-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-36/37/38
• Safety Statements: 26-36
• RTECS: RT4900000
• TSCA: Yes
• Hazardous Substances Data: 142-91-6(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 142-91-6 differently. You can refer to the following data:
1. Clear colorless liquid
2. Isopropyl palmitate is a clear, colorless to pale yellow-colored, practically odorless viscous liquid that solidifies at less than 16°C.

Uses

Different sources of media describe the Uses of 142-91-6 differently. You can refer to the following data:
1. Pharmaceutic aid (vehicle, oleaginous).
2. isopropyl palmitate is an emollient and moisturizer, it also acts as a binder and solvent. Similar to isopropyl myristate, it is produced from the combination of palmitic acid (coconut or palm oil) and isopropyl alcohol. enzymes are able to metabolize this ingredient and studies do not show allergic reactions or toxicity. Some sources indicate comedogenicity potential.
3. Isopropyl palmitate is used to formulate and evaluate the suitability of pluronic lecithin organogels containing flurbiprofen for topical application and to characterize microemulsion systems of isopropyl palmitate, water and 2:1 Brij 97, and 1-butanol by different experimental techniques.

Definition

ChEBI: A fatty acid ester obtained by the formal condensation of carboxy group of palmitic acid with propan-2-ol. Metabolite observed in cancer metabolism.

Production Methods

Isopropyl palmitate is prepared by the reaction of palmitic acid with propan-2-ol in the presence of an acid catalyst. A high-purity material is also commercially available, which is produced by enzymatic esterification at low temperatures.

General Description

Isopropyl palmitate is an analog of isopropyl myristate and an aliphatic ester used as a flavoring ingredient in food industry. It is one of the volatile compounds found in Psidium salutare fruits and boiled buckwheat flour.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Pharmaceutical Applications

Isopropyl palmitate is a nongreasy emollient with good spreading characteristics, used in topical pharmaceutical formulations and cosmetics such as: bath oils; creams; lotions; make-up; hair care products; deodorants; lip products; suntan preparations; and pressed powders. Isopropyl palmitate is an established penetration enhancer for transdermal systems. It has also been used in controlled-release percutaneous films. Table I: Uses of isopropyl palmitate

Safety

Isopropyl palmitate is widely used in cosmetics and topical pharmaceutical formulations, and is generally regarded as a relatively nontoxic and nonirritant material. LD50 (mouse, IP): 0.1 g/kg

storage

Isopropyl palmitate is resistant to oxidation and hydrolysis, and does not become rancid. It should be stored in a well-closed container, above 16°C, and protected from light.

Regulatory Status

Included in the FDA Inactive Ingredients Database (topical and transdermal preparations). Used in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

InChI:InChI=1/C19H38O2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(20)21-18(2)3/h18H,4-17H2,1-3H3

Synthetic route

1-hexadecylcarboxylic acid (57-10-3) + isopropyl alcohol (67-63-0) → palmitic acid isopropyl ester (142-91-6)

Conditions	Yield
With perchloric acid at 100℃; for 4h; Esterification;	99.74%
With alumina methanesulfonic acid at 120℃; for 0.333333h; Microwave irradiation;	97%
With toluene-4-sulfonic acid at 60℃; for 72h;	89.3%

1-hexadecylcarboxylic acid (57-10-3) + isopropyl alcohol (67-63-0) → palmitic acid isopropyl ester (142-91-6) + water (7732-18-5)

Conditions	Yield
at 140℃; under 3825.38 Torr;	A 64% B 0.06%
at 98℃; under 759.826 Torr;	A 14.04% B 0.83%

isopropyl alcohol (67-63-0) + n-hexadecanoyl chloride (112-67-4) → palmitic acid isopropyl ester (142-91-6)

Conditions	Yield
With pyridine
In pyridine
at 20℃; for 2h;
With triethylamine In dichloromethane at 0 - 4℃; for 2h;	0.9%

Hexadecanoic acid 2-(toluene-4-sulfonyloxy)-1-(toluene-4-sulfonyloxymethyl)-ethyl ester (65266-83-3) → palmitic acid isopropyl ester (142-91-6)

Conditions	Yield
With sodium tetrahydroborate

isopropyl oleate (17364-07-7, 22147-34-8, 112-11-8) + hexadecanoic acid methyl ester (112-39-0) → Methyl oleate (112-62-9) + palmitic acid isopropyl ester (142-91-6)

Conditions	Yield
With sodium methylate In hexane at 60℃; for 0.0166667h; Product distribution;

2-palmitoylglycerol (23470-00-0) → palmitic acid isopropyl ester (142-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: Py 2: NaBH4 View Scheme

2-O-palmitoyl-1,3-O-benzylideneglycerol (56599-87-2) → palmitic acid isopropyl ester (142-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: H3BO3, B(OEt)3 2: Py 3: NaBH4 View Scheme

1-hexadecylcarboxylic acid (57-10-3) → palmitic acid isopropyl ester (142-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: iodine / acetonitrile / 0.17 h / Inert atmosphere 2.1: zinc trifluoromethanesulfonate / acetonitrile / 0.5 h / 60 °C / Inert atmosphere 2.2: 5 h / 60 °C / Inert atmosphere View Scheme

C34H46O2P(1+)*I(1-) + C27H22O3P(1+)*I(1-) → palmitic acid isopropyl ester (142-91-6)

Conditions	Yield
Stage #1: C34H46O2P(1+)*I(1-) With zinc trifluoromethanesulfonate In acetonitrile at 60℃; for 0.5h; Inert atmosphere; Stage #2: C27H22O3P(1+)*I(1-) In acetonitrile at 60℃; for 5h; Inert atmosphere;	45 mg

palmitic acid isopropyl ester (142-91-6) + (-)-menthyl p-toluenesulfinate (1517-82-4) → isopropyl (RS)-α-(p-tolylsulfinyl)hexadecanoate

Conditions	Yield
With lithium cyclohexylisopropylamide In tetrahydrofuran at -60℃;	100%

palmitic acid isopropyl ester (142-91-6) + ethanolamine (141-43-5) → 2-(palmitoylamino)ethanol (544-31-0)

Conditions	Yield
With sodium ethanolate In methanol; ethanol at 60℃; for 4h; Inert atmosphere;	89%

D-ribo-phytosphingosine (554-62-1) + palmitic acid isopropyl ester (142-91-6) → N-palmitoyl-D-ribo-phytosphingosine (111149-09-8)

Conditions	Yield
With potassium hydroxide In ethanol at 55℃;	82.9%

palmitic acid isopropyl ester (142-91-6) + metformin hydrochloride (1115-70-4) → N2,N2-dimethyl-6-pentadecyl-1,3,5-triazine-2,4-diamine (66709-59-9)

Conditions	Yield
With sodium methylate In methanol for 2h; Reflux;	64%

palmitic acid isopropyl ester (142-91-6) + 1-phenylbiguanide monohydrochloride (55-57-2) → 6-pentadecyl-N2-phenyl-1,3,5-triazine-2,4-diamine (22305-30-2)

Conditions	Yield
With sodium methylate In methanol for 2h; Reflux;	42%

palmitic acid isopropyl ester (142-91-6) → isopropyl cis-6-hexadecenoate

Conditions	Yield
With cells of Rhodococcus sp. strain KSM-MT66 In water at 26℃; pH=7; Dehydrogenation;
With glutamic acid sodium salt; resting cells of a mutant; Rhodococcus sp. strain KSM-MT66 In phosphate buffer pH=7.0; Product distribution; Dehydrogenation; Microbiological reaction;

palmitic acid isopropyl ester (142-91-6) → (E)-2-((R)-1-Hydroxy-prop-2-ynyl)-hexadec-2-enoic acid (144664-37-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / LiN(i-Pr)C6H11 / tetrahydrofuran / -60 °C 2: 1.) BrMgN(i-Pr)2 / 1.) ether, 2.) ether, -40 deg C 3: NaHCO3 / benzene / 1 h / 60 °C 4: aq.KOH / methanol; diethyl ether / Ambient temperature View Scheme

palmitic acid isopropyl ester (142-91-6) → (E)-2-((R)-1-Hydroxy-prop-2-ynyl)-hexadec-2-enoic acid isopropyl ester (144582-64-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / LiN(i-Pr)C6H11 / tetrahydrofuran / -60 °C 2: 1.) BrMgN(i-Pr)2 / 1.) ether, 2.) ether, -40 deg C 3: NaHCO3 / benzene / 1 h / 60 °C View Scheme

palmitic acid isopropyl ester (142-91-6) → isoobtusilactone A

Conditions	Yield
Multi-step reaction with 5 steps 1: 100 percent / LiN(i-Pr)C6H11 / tetrahydrofuran / -60 °C 2: 1.) BrMgN(i-Pr)2 / 1.) ether, 2.) ether, -40 deg C 3: NaHCO3 / benzene / 1 h / 60 °C 4: aq.KOH / methanol; diethyl ether / Ambient temperature 5: Ag2CO3 / benzene / 80 °C View Scheme

palmitic acid isopropyl ester (142-91-6) → 2-((R)-1-Hydroxy-prop-2-ynyl)-2-((S)-toluene-4-sulfinyl)-hexadecanoic acid isopropyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / LiN(i-Pr)C6H11 / tetrahydrofuran / -60 °C 2: 1.) BrMgN(i-Pr)2 / 1.) ether, 2.) ether, -40 deg C View Scheme

Upstream product

• 67-63-0 isopropyl alcohol 
• 112-67-4 n-hexadecanoyl chloride 
• 57-10-3 1-hexadecylcarboxylic acid 
• 56599-87-2 2-O-palmitoyl-1,3-O-benzylideneglycerol 
• 23470-00-0 2-palmitoylglycerol 
• 17364-07-7 isopropyl oleate 
• 112-39-0 hexadecanoic acid methyl ester 
• 65266-83-3 Hexadecanoic acid 2-(toluene-4-sulfonyloxy)-1-(toluene-4-sulfonyloxymethyl)-ethyl ester 

Downstream Products

• 22305-30-2 6-pentadecyl-N²-phenyl-1,3,5-triazine-2,4-diamine 
• 66709-59-9 N²,N²-dimethyl-6-pentadecyl-1,3,5-triazine-2,4-diamine 
• 544-31-0 2-(palmitoylamino)ethanol 
• 111149-09-8 N-palmitoyl-D-ribo-phytosphingosine 

Related news

Production and optimization of Isopropyl palmitate (cas 142-91-6) via biocatalytic route using home‐made enzymatic catalysts09/29/2019

BACKGROUND This study investigated the use of core–shell biocatalysts, synthesized using recombinant lipase B from Candida antarctica (CALB), for the production of isopropyl palmitate and the optimization of this biocatalytic route.RESULTS Initially, three distinct core–shell biocatalysts, wer...detailed

A repeat-batch membrane bioreactor with a phase inversion for the desaturation of Isopropyl palmitate (cas 142-91-6) by a mutant Rhodococcus strain09/28/2019

A repeat-batch membrane bioreactor was constructed for the novel bioconversion of isopropyl hexadecanoate to isopropyl cis-6-hexadecenoate by a Rhodococcus mutant. The addition of glutamate, thiamine, and MgSO 4 was very effective in improving not only the rate and yield of the bioconver...detailed

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