8-Hexadecene-1,16-dicarboxylic acid
- Product Name
- 8-Hexadecene-1,16-dicarboxylic acid
- CAS No.
- 4494-16-0
- Chemical Name
- 8-Hexadecene-1,16-dicarboxylic acid
- Synonyms
- Homocivetic acid;9-Octadecenedioic acid;Octadec-9-enedioic acid;trans-9-Octadecendisure;Octadecane-9-enedioic acid;(Z)-octadec-9-enedioic acid;1,18-Octadec-9-enedioic acid;Octadec-9-ene-1,18-dioic acid;Octadecane-9-ene-1,18-dioic acid;8-Hexadecene-1,16-dicarboxylic aci
- CBNumber
- CB02283957
- Molecular Formula
- C18H32O4
- Formula Weight
- 312.44
- MOL File
- 4494-16-0.mol
8-Hexadecene-1,16-dicarboxylic acid Property
- Melting point:
- 102.5-103.5℃ (ethyl acetate )
- Boiling point:
- 426.4±20.0 °C(Predicted)
- Density
- 1.012±0.06 g/cm3(Predicted)
- vapor pressure
- 0-0.36Pa at 20℃
- storage temp.
- Sealed in dry,Room Temperature
- form
- Solid
- pka
- 4.48±0.10(Predicted)
- Appearance
- White to off-white Solid
- LogP
- 2.4-5.91 at 23℃ and pH2
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 6200AB
- Product name
- Octadec-9-enedioicacid
- Packaging
- 250mg
- Price
- $366
- Updated
- 2021/12/16
- Product number
- LIP0003805
- Product name
- OCTADEC-9-ENEDIOIC ACID
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $498.92
- Updated
- 2021/12/16
- Product number
- 095300
- Product name
- Octadec-9-enedioic acid
- Purity
- 95+%
- Packaging
- 250mg
- Price
- $591
- Updated
- 2021/12/16
- Product number
- 095300
- Product name
- Octadec-9-enedioic acid
- Purity
- 95+%
- Packaging
- 1g
- Price
- $1311
- Updated
- 2021/12/16
- Product number
- CD13012884
- Product name
- Octadec-9-enedioicacid
- Purity
- 95+%
- Packaging
- 1g
- Price
- $579
- Updated
- 2021/12/16
8-Hexadecene-1,16-dicarboxylic acid Chemical Properties,Usage,Production
Uses
Octadec-9-enedioic Acid is a potential antioxidant and antimicrobial agent.
Synthesis
112-80-1
4494-16-0
5557-31-3
Oleic acid ((3b), 89 g (90%, 0.315 mol) was transferred via syringe into a 250 mL three-necked round-bottomed flask and vented with nitrogen for 0.5 hours. Subsequently, 1,3-bis(2,4,6-trimethylphenyl)-2-(imidazolidinyl)(dichlorophenylmethylene)(tricyclohexylphosphine)ruthenium (second-generation Grubbs catalyst, 2,267 mg, 0.315 mmol) was added; the reaction required no solvent. The reaction mixture was stirred at 45 °C using a mechanical stirrer and a white precipitate was formed after about 5 min. After the reaction was carried out for 24 h, about 10 mg of the crude product was removed and transferred to a 2 mL dram vial. To the crude diacid product (5b, Equation 1), 1 mL of methanol and two drops of concentrated sulfuric acid were added, and the mixture was heated at 80°C for 0.5 h. (Christie, W.W., Lipid Analysis: Isolation, Separation, Identification and Structural Analysis of Lipids, Oxford, NY Pergamon Press (1982)). The reaction mixture was subsequently quenched with 2 mL of 1M Na2CO3, extracted with ether (3 x 2 mL), and the combined ether layers were washed with water (3 x 2 mL). The organic layer was dried with MgSO4, filtered and the solvent was removed under reduced pressure, and the methylated dicarboxylic acid 5b was characterized by GC/MS (retention time = 14.2 min) to give [M]+ m/z 340 (calculated value, for 5b, [M]+ m/z = 340.26). The remaining crude product was quenched with ethyl vinyl ether (20 mL) and the excess ether was removed under reduced pressure. The residue was recrystallized twice from a mixture of hexane (300 mL) and ethyl acetate (50 mL) to give pure 1,18-octadeca-9-enedioic acid (5b, Equation 1) as a white solid with a melting point of 97.5-98.5°C (literature value 88°C (Van Dam, P.B., et al., J. Am. Oil Chem. Soc., 51. 389-391 (1974)). Isolated yield: 35 g (71%). 1H NMR of 1,18-octadeca-9-enedioic acid (CD3OD, 400 MHz): δ 5.39 (m, -CH=CH-, 2H), 2.28 (t, J=7.2 Hz, -CH2CO2H, 4H), 1.98 (m, 4H), 1.60 (m, 4H), 1.32 (m, 16H) .13C NMR (CD3OD, 100 MHz): δ177.8 (s, CO2H), 131.6 (s, CH=CH), 35.1 (s), 33.7 (s), 30.8 (s), 30.4 (s), 30.3 (s), 30.2 (s), 26.2 (s).
References
[1] JAOCS, Journal of the American Oil Chemists' Society, 2006, vol. 83, # 7, p. 629 - 634
[2] Patent: US7534917, 2009, B1. Location in patent: Page/Page column Sheet 2/6; 6-8; 16; 18
[3] Patent: EP1251135, 2002, A2. Location in patent: Page 16
[4] Journal of the American Chemical Society, 2012, vol. 134, # 33, p. 13716 - 13729
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View Lastest Price from 8-Hexadecene-1,16-dicarboxylic acid manufacturers
- Product
- 8-Hexadecene-1,16-dicarboxylic acid 4494-16-0
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10000KGS
- Release date
- 2025-11-21
- Product
- 9-Octadecenedioic acid 4494-16-0
- Price
- US $2.20-8.80/kg
- Min. Order
- 1kg
- Purity
- 99%min
- Supply Ability
- 1000kg
- Release date
- 2025-06-13
- Product
- Octadec-9-enedioic acid 4494-16-0
- Price
- US $1.00/kg
- Min. Order
- 1g
- Purity
- 99%
- Supply Ability
- 100KG
- Release date
- 2018-12-25