cis-9-Hexadecenoic Acid - Moligand™, 10mM in DMSO , CAS No.373-49-9

CAS: 373-49-9 Cat. No.: C423680 Molecular Weight: 254.41 Beilstein Registry Number: 1725389 EC Number: 206-765-9

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

CHEBI:28716 | MFCD00004437 | cis-Delta(9)-hexadecenoic acid | (Z)-9-hexadecenoic acid | (Z)-Hexadec-9-enoicacid | 5,8,11,14-Eicosatetraenoic acid, methyl ester, cis- | Hexadecenoate | PALMITOLEIC ACID (CONSTITUENT OF SPIRULINA) [DSC] | cis-.delta.9-Hexade

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Application

Drug Delivery, Surface Modification, PEGylation of Protein, Peptide & Oligo

Overview

Product 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)

Specifications

Synonyms

CHEBI:28716 | MFCD00004437 | cis-Delta(9)-hexadecenoic acid | (Z)-9-hexadecenoic acid | (Z)-Hexadec-9-enoicacid | 5, 8, 11, 14-Eicosatetraenoic acid, methyl ester, cis- | Hexadecenoate | PALMITOLEIC ACID (CONSTITUENT OF SPIRULINA) [DSC] | cis-.delta.9-Hexade

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

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

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Canonical Smiles: CCCCCCC=CCCCCCCCC(=O)O
• IUPAC Name: (Z)-hexadec-9-enoic acid
• InChIKey: SECPZKHBENQXJG-FPLPWBNLSA-N
• 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-
• Isomeric SMILES: CCCCCC/C=C\CCCCCCCC(=O)O
• WGK Germany: 1
• Molecular Weight: 254.41
• Beilstein: 1725389
• Reaxy-Rn: 1781015
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1781015&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty acids and conjugates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Long-chain fatty acids
• Alternative Parents: Unsaturated fatty acids Straight chain fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Long-chain fatty acid - Unsaturated fatty acid - Straight chain fatty acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
• External Descriptors: Unsaturated fatty acids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

Discover Target: PPARG

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)

Discover Target: PPARA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TERT Tchem Telomerase reverse transcriptase (2428 Activities)

Discover Target: TERT

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FFAR3 Tchem Free fatty acid receptor 3 (304 Activities)

Discover Target: FFAR3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Trypsin (394 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

Discover Target: Ppard

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

Discover Target: Ptpn1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus aureus (210822 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Geobacillus stearothermophilus (181 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus subtilis (32866 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Enterococcus faecalis (29875 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus cereus (7522 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: air sensitive，heat sensitive
• Refractive Index: 1.457
• Flash Point(°F): 143.6 °F
• Flash Point(°C): 62℃
• Boil Point(°C): 175°C/15mmHg
• Melt Point(°C): 1°C
• Molecular Weight: 254.410 g/mol
• XLogP3: 6.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 13
• Exact Mass: 254.225 Da
• Monoisotopic Mass: 254.225 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 209.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Zhu Yanli, Wang Jikai, Fu Chengxiao, Liu Shuangquan, Awasthi Pragati, Zeng Pengfei, Chen Danjun, Sun Yiyang, Mo Ziyi, Liu Hailing.  (2023)  Temporally and spatially resolved molecular profiling in fingerprint analysis using indium vanadate nanosheets-assisted laser desorption ionization mass spectrometry.  JOURNAL OF NANOBIOTECHNOLOGY,  21  (1): (1-15).  [PMID:38072936] [10.1186/s12951-023-02239-w]

2. Jian Zhang, Zesen Zhang, Ting Jiang, Zhenyu Zhang, Wenjing Zhang, Wei Xu.  (2023)  Rapidly identifying and quantifying of unsaturated lipids with carbon‐carbon double bond isomers by photoepoxidation.  TALANTA,      [PMID:37141821] [10.1016/j.talanta.2023.124575]

3. LI Ying, LEE Xiangjun, GUO Jianfeng, FENG Jingjing, XU Chenshuai, BAI Yujie, GUO Shiwei, WANG Fang.  (2023)  Study on the enrichment of palmitoleic acid in Sn-2 monoester from sea-buckthorn fruit oil.  Food Science and Technology,      [PMID:] [10.1590/fst.107722]

4. Chenhui Gu, Xuewen Hu, Baixi Shan, Xiaojing Wu, Jun Chen.  (2023)  Targeted and non-targeted metabolomics uncovering the effects of Er-Miao-Wan formula on rats with hyperuricemia.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:36731256] [10.1016/j.jpba.2023.115246]

5. Jie Cheng, Yuling Li, Yunjun Wang, Jing Zhang, Tuanqi Sun, Li Zhang, Yinlong Guo.  (2022)  Quaterization Derivatization with Bis(Pyridine) Iodine Tetrafluoroboride: High-Sensitivity Mass Spectrometric Analysis of Unsaturated Fatty Acids in Human Thyroid Tissues.  ANALYTICAL CHEMISTRY,      [PMID:35916214] [10.1021/acs.analchem.2c01519]

6. Jieyuan Wu, Wei Chen, Yutong Zhang, Xuanxuan Zhang, Jian-Ming Jin, Shuang-Yan Tang.  (2020)  Metabolic Engineering for Improved Curcumin Biosynthesis in Escherichia coli.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:32864959] [10.1021/acs.jafc.0c04276]

7. Liu Xiaohong, Zeng Xin, Chen Xuanming, Luo Ruixi, Li Linzhao, Wang Chengshi, Liu Jingping, Cheng Jingqiu, Lu Yanrong, Chen Younan.  (2019)  Oleic acid protects insulin-secreting INS-1E cells against palmitic acid-induced lipotoxicity along with an amelioration of ER stress.  ENDOCRINE,  64  (3): (512-524).  [PMID:30778898] [10.1007/s12020-019-01867-3]

8. Kok Bing Tan, Yiping Liu, Youting Wang, Sajid Ali, Wendong Wang, Jingru Li, Longmei Shang, Xing Yan, Xiaodong Zhang, Guowu Zhan.  (2024)  Catalytic deoxygenation of stearic acid into olefins over Pt catalysts supported on MOF-derived metal oxides.  Catalysis Science & Technology,  14  (12): (3436-3447).  [PMID:] [10.1039/D4CY00189C]

9. Guo XiaoYu, Zhou Jianglu, Yu Hong, Cao Han, Li Xia, Hu Qing, Yu YunQiu.  (2024)  Serum lipidomic study of long-chain fatty acids in psoriasis patients prior to and after anti-IL-17A monoclonal antibody treatment by quantitative GC‒MS analysis with in situ extraction.  Lipids in Health and Disease,  23  (1): (1-15).  [PMID:38185620] [10.1186/s12944-023-01999-6]