373-49-9

Basic information

• Product Name: PALMITOLEIC ACID
• Synonyms: CIS-9-HEXADECENOIC ACID;DELTA 9 CIS HEXADECENOIC ACID;C16:1 (CIS-9) ACID;9-HEXADECENOIC ACID;RARECHEM AL BE 0686;PALMITOLEIC ACID;(Z)-9-hexadecenoic acid;(Z)-Palmitoleic acid
• CAS NO: 373-49-9
• Molecular Formula: C₁₆H₃₀O₂
• Molecular Weight: 254.41
• EINECS: 206-765-9
• Product Categories: Biochemistry;Higher Fatty Acids & Higher Alcohols;Unsaturated Higher Fatty Acids;NULL
• Mol File: 373-49-9.mol
• Article Data: 17

Chemical Properties

• Melting Point: 0.5 °C
• Boiling Point: 162 °C (0.6 mmHg)
• Flash Point: 62 °C
• Appearance: Clear/Liquid
• Density: 0.894
• Vapor Pressure: 2.82E-06mmHg at 25°C
• Refractive Index: 1.457-1.459
• Storage Temp.: −20°C
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 4.78±0.10(Predicted)
• BRN: 1725389
• CAS DataBase Reference: PALMITOLEIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: PALMITOLEIC ACID(373-49-9)
• EPA Substance Registry System: PALMITOLEIC ACID(373-49-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 373-49-9(Hazardous Substances Data)

Usage

Description

Palmitoleic acid, or (Z)-9-hexadecenoic acid, is an omega - 7 mono unsaturated fatty acid with the formula CH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue. It is present in all tissues, but generally found in higher concentrations in the liver. It is biosynthesized from palmitic acid by the action of the enzyme delta-9 desaturase. A beneficial fatty acid, it has been shown to increase insulin sensitivity by suppressing inflammation, as well as inhibit the destruction of insulin-secreting pancreatic beta cells.

Chemical Properties

Different sources of media describe the Chemical Properties of 373-49-9 differently. You can refer to the following data:
1. clear liquid
2. PALMITOLEIC ACID, Also called cis-9-hexa decanoic acid, formula CH3(CH2)5CH:CH(CH2)7COOH. This is an unsaturated fatty acid found in nearly every fat, especially in marine oils (15–20%). At room temperature, it is a colorless liquid. Insoluble in water; soluble in alcohol and ether. Insoluble in water; soluble in alcohol and ether. Combustible.

Occurrence

Palmitoleic acid can be abbreviated as 16:1Δ9. Dietary sources of palmitoleic acid include a variety of animal oils, vegetable oils, and marine oils. Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophae rhamnoides) are botanical sources with high concentrations, containing 17 % and 40 % of palmitoleic acid, respectively.

Uses

Different sources of media describe the Uses of 373-49-9 differently. You can refer to the following data:
1. Palmitoleic Acid is a polyunsaturated fatty acid which contributes to reduced protein oxidation in mammals when added as a dietary supplement.
2. Palmitoleic acid is used in organic synthesis, and as a standard in chromatographic analysis.
3. Palmitoleic Acid is a polyunsaturated fatty acid which contributes to reduced protein oxidation in mammals.

Definition

ChEBI: A hexadecenoic acid with a cis-double bond at position C-9.

General Description

Palmitoleic acid is a monounsaturated fatty acid found in macadamia oil and also in blood plasma. In the human body it is produced via endogenous fat synthesis.

Biochem/physiol Actions

Palmitoleic acid is a 16-carbon, omega-7, monounsaturated fatty acid that is enriched in the triglycerides of human adipose tissue and in liver.

InChI:InChI=1/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-

Upstream product

• 725720-60-5 15-ethoxy-pentadecane-7,8-diol 
• 57491-64-2 16-Iodo-(Z)-9-hexadecenoic acid 
• 533-87-9 erythro-9,10,16-trihydroxyhexadecanoic acid 
• 111-62-6 oleic acid ethyl ester 
• 8001-23-8 safflower oil 
• 1120-25-8 (Z)-9-hexadecenoic acid methyl ester 
• 29823-21-0 Ethyl 8-bromooctanoate 
• 17696-11-6 8-bromooctanoic acid 
• 2027-46-5 erythro-9.10-Dihydroxyhexadecanoic acid 
• 56219-10-4 cis-9-hexadecenoic acid ethyl ester 
• 111-71-7 heptanal 
• 57-10-3 1-hexadecylcarboxylic acid 
• 10378-01-5 palmitoleyl alcohol 
• 56219-04-6 (Z)-9-hexadecenal 

Downstream Products

• 40853-88-1 (Z)-hexadec-9-enylamine 
• 29242-09-9 9,10-dihydroxy-hexadecanoic acid 
• 2027-46-5 (+/-)-threo-9,10-Dihydroxy-hexadecansaeure 
• 61393-51-9 hexadecen-(7c)-oic acid-⁽¹⁶⁾-(4-bromo-phenacyl ester) 
• 123-99-9 azelaic acid 
• 111-71-7 heptanal 
• 111-14-8 oenanthic acid 
• 1120-25-8 (Z)-9-hexadecenoic acid methyl ester 
• 40426-22-0 ( Z )-hexadec-9-enoyl chloride 
• 57-10-3 1-hexadecylcarboxylic acid 
• 5070-03-1 (9Z,12Z)-9,12-hexadecadienoic acid 
• 649764-97-6 (Z)-Hexadec-9-enoic acid 3-(tert-butyl-diphenyl-silanyloxymethyl)-5-((Z)-hexadec-9-enoyloxy)-pentyl ester 
• 112-62-9 octadec-9-enoic acid methyl ester 
• 29972-79-0 methyl 11-dodecenoate 

Relevant articles and documents

Maternal obesity results in decreased syncytiotrophoblast synthesis of palmitoleic acid, a fatty acid with anti-inflammatory and insulin-sensitizing properties

The fetus is dependent on delivery of fatty acids (FAs) by the syncytiotrophoblast, the transporting epithelium of the human placenta. Obese pregnant women have dyslipidemia; however, whether obesity impacts placental lipid transport and metabolism remains to be fully established. Palmitoleic acid (POA), an FA with antiinflammatory and insulin-sensitizing properties, is synthesized from palmitic acid (PA) catalyzed by stearoyl-coenzyme A desaturase (SCD) activity. We hypothesized that the uptake and incorporation of FAs and POA synthesis are reduced in primary human trophoblasts (PHTs) isolated from pregnancies complicated by maternal obesity. Villous cytotrophoblasts were isolated from 7 placentas of obese [body mass index (BMI) = 37.5 ± 1.9] and 12 normal (BMI = 23.6 ± 0.6) mothers. FA uptake and incorporation were assessed using uniformly labeled (U[13C])–FA mixtures of PA, oleic acid (OA), linoleic acid, and docosahexaenoic acid. Cellular [13C] FAs were quantified both in total cellular lipids and in lipid classes by GC-MS. Uptake and incorporation of [13C] FAs in total cellular lipids were not different in PHTs isolated from obese mothers compared with normal mothers. Only the concentration of OA was increased in the triglyceride fraction (P 13C]-PA treatment, demonstrating SCD activity in PHT cells. Labeled POA content and the POA:PA ratio were significantly lower in PHTs isolated from placentas of obese mothers compared with normal, healthy controls. Decreased syncytiotrophoblast POA synthesis may contribute to insulin resistance and low-grade inflammation in the mother, placenta, or fetus (or a combination of the 3) in pregnancies complicated by obesity.—Ferchaud-Roucher, V., Barner, K., Jansson, T., Powell, T. L. Maternal obesity results in decreased syncytiotrophoblast synthesis of palmitoleic acid, a fatty acid with anti-inflammatory and insulin-sensitizing properties. FASEB J. 33, 6643–6654 (2019). www.fasebj.org.

Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2

It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50 of 9 μM and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GlyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 μM. This novel class of compounds show considerable promise as a first generation of GlyT2 transport inhibitors.

ESTERAMINES AND DERIVATIVES FROM NATURAL OIL METATHESIS

Esteramine compositions and their derivatives are disclosed. The esteramines comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a tertiary alkanolamine. Derivatives made by quaternizing, sulfonating, alkoxylating, sulfating, and/or sulfitating the esteramines are also disclosed. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The esteramines and derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.