28290-73-5

Basic information

• Product Name: (7Z,10Z)-Hexadecadienoic acid
• Synonyms: (7Z,10Z)-Hexadecadienoic acid;7Z,10Z-Hexadecadienoic acid
• CAS NO: 28290-73-5
• Molecular Formula: C₁₆H₂₈O₂
• Molecular Weight: 252.39
• Mol File: 28290-73-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 346.8°C at 760 mmHg
• Flash Point: 243.7°C
• Appearance: /
• Density: 0.919g/cm³
• Vapor Pressure: 9.92E-06mmHg at 25°C
• Refractive Index: 1.479
• CAS DataBase Reference: (7Z,10Z)-Hexadecadienoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (7Z,10Z)-Hexadecadienoic acid(28290-73-5)
• EPA Substance Registry System: (7Z,10Z)-Hexadecadienoic acid(28290-73-5)

Safety Data

• Hazardous Substances Data: 28290-73-5(Hazardous Substances Data)

Usage

Description

(7Z,10Z)-Hexadecadienoic acid, also known as (7Z,10Z)-7,10-Hexadecadienoic Acid, is a polyunsaturated fatty acid that is a minor constituent of volatile oils from Gliomastix murorum and Pichia guilliermondii. It is characterized by having two double bonds located at positions 7 and 10 (the 7Z,10Z-geoisomer) and possesses antimicrobial activity.

Uses

Used in Antimicrobial Applications:
(7Z,10Z)-Hexadecadienoic acid is used as an antimicrobial agent for its ability to inhibit the growth of various microorganisms. Its presence in volatile oils from certain organisms contributes to their natural defense mechanisms against harmful microbes.
Used in Pharmaceutical Industry:
(7Z,10Z)-Hexadecadienoic acid is used as a potential therapeutic agent for its antimicrobial properties. It can be explored for the development of new drugs or treatments targeting bacterial and fungal infections, particularly those resistant to conventional antibiotics.
Used in Cosmetics Industry:
(7Z,10Z)-Hexadecadienoic acid can be used as an ingredient in the cosmetics industry, where its antimicrobial properties can help maintain the cleanliness and safety of products, reducing the risk of contamination and promoting a longer shelf life.
Used in Food Industry:
(7Z,10Z)-Hexadecadienoic acid can be utilized in the food industry as a natural preservative to extend the shelf life of perishable products and prevent the growth of harmful bacteria and fungi.
Used in Agricultural Industry:
(7Z,10Z)-Hexadecadienoic acid can be employed in the agricultural industry as a natural antimicrobial agent to protect crops from bacterial and fungal infections, reducing the need for synthetic pesticides and promoting sustainable farming practices.

InChI:InChI=1/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h6-7,9-10H,2-5,8,11-15H2,1H3,(H,17,18)/b7-6-,10-9-

Synthetic route

(7Z",10Z")-hexadecadienoic acid methyl ester (18829-90-8) → (7Z,10Z)-7,10-hexadecadienoic acid (28290-73-5)

Conditions	Yield
With sodium hydroxide In methanol; water at 20℃; for 8h; Inert atmosphere;	64%

(7Z,10Z)-hexadeca-7,10-dien-1-ol (121695-19-0) → (7Z,10Z)-7,10-hexadecadienoic acid (28290-73-5)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In water; acetone at 0℃; for 0.5h;

<(3Z)-nonen-1-yl>triphenylphosphonium iodide (72297-07-5) → (7Z,10Z)-7,10-hexadecadienoic acid (28290-73-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C / under N2 2: 30percent H3PO4 / methanol / 5 h / Ambient temperature 3: CrO3, conc H2SO4 / H2O; acetone / 0.5 h / 0 °C View Scheme

2-[((7Z,10Z)-Hexadeca-7,10-dienyl)oxy]-tetrahydro-pyran (123160-44-1) → (7Z,10Z)-7,10-hexadecadienoic acid (28290-73-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 30percent H3PO4 / methanol / 5 h / Ambient temperature 2: CrO3, conc H2SO4 / H2O; acetone / 0.5 h / 0 °C View Scheme

oct-2-ynoic acid (5663-96-7) → (7Z,10Z)-7,10-hexadecadienoic acid (28290-73-5)

Conditions

Yield

Multi-step reaction with 6 steps 1: diethyl ether 2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / -5 °C 3: potassium carbonate; potassium hydroxide / acetone; water / 1.5 h / 0 °C / Inert atmosphere 4: sodium iodide; potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere 5: nickel(II) acetate tetrahydrate; sodium tetrahydroborate; ethylenediamine; hydrogen / ethanol / 1 h / 10 °C 6: sodium hydroxide / water; methanol / 8 h / 20 °C / Inert atmosphere View Scheme

methyl 2-octynoate (111-12-6) → (7Z,10Z)-7,10-hexadecadienoic acid (28290-73-5)

Conditions

Yield

Multi-step reaction with 5 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / -5 °C 2: potassium carbonate; potassium hydroxide / acetone; water / 1.5 h / 0 °C / Inert atmosphere 3: sodium iodide; potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere 4: nickel(II) acetate tetrahydrate; sodium tetrahydroborate; ethylenediamine; hydrogen / ethanol / 1 h / 10 °C 5: sodium hydroxide / water; methanol / 8 h / 20 °C / Inert atmosphere View Scheme

2-octyn-1-ol (20739-58-6) → (7Z,10Z)-7,10-hexadecadienoic acid (28290-73-5)

Conditions

Yield

Multi-step reaction with 4 steps 1: potassium carbonate; potassium hydroxide / acetone; water / 1.5 h / 0 °C / Inert atmosphere 2: sodium iodide; potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere 3: nickel(II) acetate tetrahydrate; sodium tetrahydroborate; ethylenediamine; hydrogen / ethanol / 1 h / 10 °C 4: sodium hydroxide / water; methanol / 8 h / 20 °C / Inert atmosphere View Scheme

1-(p-tolylsulfonyloxy)oct-2-yne (57342-29-7) → (7Z,10Z)-7,10-hexadecadienoic acid (28290-73-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium iodide; potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere 2: nickel(II) acetate tetrahydrate; sodium tetrahydroborate; ethylenediamine; hydrogen / ethanol / 1 h / 10 °C 3: sodium hydroxide / water; methanol / 8 h / 20 °C / Inert atmosphere View Scheme

Dimethyldisulphide (624-92-0) + (7Z,10Z)-7,10-hexadecadienoic acid (28290-73-5) → 6-[3-Methylsulfanyl-5-(1-methylsulfanyl-hexyl)-tetrahydro-thiophen-2-yl]-hexanoic acid + 7-Methylsulfanyl-7-[4-(1-methylsulfanyl-hexyl)-thietan-2-yl]-heptanoic acid + 6-(3,5-Bis-methylsulfanyl-6-pentyl-tetrahydro-thiopyran-2-yl)-hexanoic acid + 7-Methylsulfanyl-7-(4-methylsulfanyl-5-pentyl-tetrahydro-thiophen-2-yl)-heptanoic acid

Conditions	Yield
With iodine In diethyl ether at 53℃; for 24h;

(7Z,10Z)-7,10-hexadecadienoic acid (28290-73-5) → all-cis-1,6,9-Pentadecatrien (77388-07-9)

Conditions	Yield
With pyridine; lead(IV) acetate; copper diacetate In benzene for 2h; Heating;

(7Z,10Z)-7,10-hexadecadienoic acid (28290-73-5) → (6Z,9Z)-6,9-Pentadecadienal

Conditions	Yield
With LCA(long chain aldehydes)-forming activity in Ulva pertusa fronds solubilized by Triton X-100 at 35℃; for 0.25h;

Upstream product

• 57342-29-7 1-(p-tolylsulfonyloxy)oct-2-yne 
• 20739-58-6 2-octyn-1-ol 
• 111-12-6 methyl 2-octynoate 
• 18829-90-8 (7Z,10Z)-hexadecadienoic acid methyl ester 
• 5663-96-7 oct-2-ynoic acid 
• 72297-07-5 <(3Z)-nonen-1-yl>triphenylphosphonium iodide 
• 123160-44-1 2-[((7Z,10Z)-Hexadeca-7,10-dienyl)oxy]-tetrahydro-pyran 
• 121695-19-0 (7Z,10Z)-hexadeca-7,10-dien-1-ol 

Relevant articles and documents

Synthesis of the ω6 (5z,8z)-tetradecadienoic and (7z,10z)-hexadecadienoic polyene fatty acids

An approach using acetylenes was used and optimized to synthesize rare natural ω6 polyene fatty acids. The key synthetic step was cross-coupling of a propargyl derivative with a terminal acetylene in the presence of equimolar amounts of Cu(I).