1120-25-8

Basic information

• Product Name: PALMITOLEIC ACID METHYL ESTER
• Synonyms: METHYL CIS-9-HEXADECENOATE;METHYL PALMITOLEATE;C16:1 (CIS-9) METHYL ESTER;DELTA 9 CIS HEXADECENOIC ACID METHYL ESTER;CIS-9-HEXADECENOIC ACID METHYL ESTER;PALMITOLEIC ACID METHYL ESTER;Methyl (9Z)-9-hexadecenoate;methyl palmitioleate
• CAS NO: 1120-25-8
• Molecular Formula: C₁₇H₃₂O₂
• Molecular Weight: 268.43
• EINECS: 214-303-2
• Mol File: 1120-25-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: −0.5-0.5 °C(lit.)
• Boiling Point: 180-183 °C/1 mmHg(lit.)
• Flash Point: 113 °C
• Appearance: /Liquid
• Density: 0.875 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.01E-06mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: -0°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• BRN: 1726111
• CAS DataBase Reference: PALMITOLEIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: PALMITOLEIC ACID METHYL ESTER(1120-25-8)
• EPA Substance Registry System: PALMITOLEIC ACID METHYL ESTER(1120-25-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 1
• Hazardous Substances Data: 1120-25-8(Hazardous Substances Data)

Usage

Description

Palmitoleic acid methyl ester is an ester version of palmitoleic acid , an ω-7 monounsaturated fatty acid that is a common constituent of the triglycerides of human adipose tissue. Palmitoleic acid-based diets raise low-density lipoprotein (LDL) cholesterol and lower high-density lipoprotein (HDL) cholesterol, even when dietary intake of cholesterol is maintained at a low level. Methyl esters of fatty acids are commonly used for the formulation of fatty acid-containing diets and dietary supplements.

Uses

Methyl Palmitoleate is used as a component in the preparation of a biodiesel fuels.

Definition

ChEBI: A fatty acid methyl ester obtained from the formal condensation of methanol and palmitoleic acid.

General Description

Methyl palmitoleate is a major component of biodiesel having low temperature property, which is found to be more advantageous than methyl oleate.

InChI:InChI=1/C17H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19-2/h8-9H,3-7,10-16H2,1-2H3/b9-8-

Upstream product

• 16045-88-8 boron trifluoride methanol complex 
• 67-56-1 methanol 
• 111-66-0 oct-1-ene 
• 25601-41-6 methyl 9-decenoate 
• 373-49-9 cis-9-hexadecenoic acid 
• 79-20-9 acetic acid methyl ester 
• 2553-17-5 azelaic acid semialdehyde 
• 533-87-9 9,10,16-trihydroxyhexadecanoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 25258-24-6 1-tetrahydropyranyloxy-n-9-hexadecyn 
• 50816-19-8 8-bromooctanol 
• 89155-39-5 .9-hexadecynoic acid 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 89199-88-2 C₁₇H₃₀O₂ 

Downstream Products

• 10030-74-7 palmitelaidic acid methyl ester 
• 373-49-9 cis-9-hexadecenoic acid 
• 37515-61-0 monopalmitolein 
• 4675-60-9 (±)-cis-9,10-methylenehexadecanoic acid 
• 19102-92-2 dimethyl heptadecane-1,17-dioate 
• 56219-04-6 (Z)-9-hexadecenal 
• 10152-61-1 (±)-methyl cis-9,10-methylenehexadecanoate 
• 123-99-9 azelaic acid 
• 111-14-8 oenanthic acid 
• 334-48-5 1-decanoic acid 
• 10378-01-5 palmitoleyl alcohol 
• 2027-46-5 (+/-)-threo-9,10-Dihydroxy-hexadecansaeure 
• 29242-09-9 9,10-dihydroxy-hexadecanoic acid 

Relevant articles and documents

Potent Anti-HIV Ingenane Diterpenoids from Euphorbia ebracteolata

Two new (1 and 2) and 14 known (3-16) ingenane diterpenoids were isolated from the roots of Euphorbia ebracteolata by bioassay-guided fractionation together with UPLC-MSn analysis. The absolute configurations of the new diterpenoids were established from electronic circular dichroism (ECD) data and ECD calculations. Except for ingenol (16), the ingenane diterpenoids with long aliphatic chain substituents (1-15) exhibited potent activities against HIV-1, with IC50 values of 0.7 to 9.7 nM and selectivity index values of 96.2 to 20 263. From the results, it was concluded that long aliphatic chain substituents are required for the enhanced anti-HIV activity of ingenane diterpenoids.

Structural identification of antibacterial lipids from Amazonian palm tree endophytes through the molecular network approach

A library of 197 endophytic fungi and bacteria isolated from the Amazonian palm tree Astrocaryum sciophilum was extracted and screened for antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Four out of five antibacterial ethyl acetate extracts were also cytotoxic for the MRC-5 cells line. Liquid chromatography coupled to tandem mass spectrometry (UPHLC-HRMS/MS) analyses combined with molecular networking data processing were carried out to allow the identification of depsipeptides and cyclopeptides responsible for the cytotoxicity in the dataset. Specific ion clusters from the active Luteibacter sp. extract were also highlighted using an MRSA activity filter. A chemical study of Luteibacter sp. was conducted leading to the structural characterization of eight fatty acid exhibiting antimicrobial activity against MRSA in the tens of μg/mL range.

Insight into isolation and elucidation of cytotoxic ergostanoids from the mushroom Sarcosphaera crassa (Santi) Pouzar: An edible mushroom

Sarcosphaera crassa is a mushroom consumed in Europe and Anatolia after being cooked well. The cytotoxic activity of the extracts of unbaked S. crassa against MCF7, HT29, HeLa cancer cell lines and toxicity against PDF fibroblast healthy cell lines were studied using MTT assay. Acetone and methanol extracts of the mushroom exhibited significant cytotoxic activity. Further investigation of cytotoxic extracts afforded two new fatty acid sterols (1–2), a new ergosterol glycoside (4), and seven known compounds, including a fatty acid sterol (3), a steroid glycoside (5), two ergostanoids (6–7) and three sugars (8–10). These compounds were identified as brassicasteryl heptadecanoate (1), brassicasteryl palmitoleate (2), brassicasteryl linoleate (3), brassicasterol β-?-xylofuranoside (4), brassicasterol β-?-glucoside (5), brassicasterol (6), ergosterol-endoperoxide (7), mannitol (8), erythritol (9) and turanose (10). Among them, 7 exhibited a moderate cytotoxic activity against HeLa (IC50: 70.1 ± 2.0 μg/mL) and high activity against HT29 (IC50: 38.8 ± 0.9 μg/mL), and MCF7 (IC50: 62.9 ± 1.3 μg/mL) cancer cell lines. Compounds 4, 5, and 6 also exhibited significant cytotoxic activity against HT29 and MCF7. Moreover, all compounds exhibited weak toxicity against PDF healthy cell lines. This study indicates the potential use of Sarcosphaera crassa as a natural source of cytotoxic ergostanoids, which can be considered a dietary supplement for cancer prevention.

PRODUCTION OF FATTY OLEFIN DERIVATIVES VIA OLEFIN METATHESIS

In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.