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About This Item
Linear Formula:
CH3(CH2)5CH=CH(CH2)7COOH
CAS Number:
Molecular Weight:
254.41
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
EC Number:
206-765-9
Beilstein/REAXYS Number:
1725389
MDL number:
biological source
Macadamia integrifolia
assay
≥98.5% (GC)
form
liquid
refractive index
n20/D 1.457 (lit.)
bp
162 °C/0.6 mmHg (lit.)
mp
0.5 °C (lit.)
density
0.895 g/mL at 20 °C (lit.)
functional group
carboxylic acid, oleic acid
lipid type
unsaturated FAs
shipped in
ambient
storage temp.
−20°C
SMILES string
CCCCCC\C=C/CCCCCCCC(O)=O
InChI
1S/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-
InChI key
SECPZKHBENQXJG-FPLPWBNLSA-N
Application
Palmitoleic acid has been used:
- to supplement Minimum Essential Media alpha (MEMα) to culture mouse spermatogonial stem cells (SSCs)
- as a component of a defined serum-free medium for the long-term propagation of SSCs
- in Dulbecco′s Modified Eagle Medium (DMEM) in the media for fatty acid treatment to assure a physiologic ratio between bound and unbound free fatty acid (FFA)
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.
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signalword
Warning
hcodes
Hazard Classifications
Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
flash_point_f
143.6 °F - closed cup
flash_point_c
62 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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Yuko Akazawa et al.
Journal of hepatology, 52(4), 586-593 (2010-03-09)
Saturated free fatty acids induce hepatocyte lipoapoptosis. This lipotoxicity involves an endoplasmic reticulum stress response, activation of JNK, and altered expression and function of Bcl-2 proteins. The mono-unsaturated free fatty acid palmitoleate is an adipose-derived lipokine which suppresses free fatty
Dariush Mozaffarian et al.
The American journal of clinical nutrition, 97(4), 854-861 (2013-02-15)
Dairy consumption is linked to a lower risk of type 2 diabetes, but constituents responsible for this relation are not established. Emerging evidence suggests that trans-palmitoleate (trans 16:1n-7), a fatty acid in dairy and also partially hydrogenated oils, may be
Geng Zong et al.
The American journal of clinical nutrition, 96(5), 970-976 (2012-09-28)
Palmitoleic acid has been shown to regulate adipokine expression and systemic metabolic homeostasis in animal studies. However, its association with human metabolic diseases remains controversial. We aimed to investigate associations of erythrocyte palmitoleic acid with adipokines, inflammatory markers, and metabolic
