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Chemistry
Organic Building Blocks
Carboxylic Acids
trans-8-Methyl-6-nonenoic acid, predominantly
Chemistry
Pharmaceutical Intermediate
Organic Building Blocks
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Carboxylic Acids
Aliphatic Chain Hydrocarbons Alkenes Capsaicin

[ CAS No. 59320-77-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 59320-77-3
Chemical Structure| 59320-77-3
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Quality Control of [ 59320-77-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
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Product Details of [ 59320-77-3 ]

CAS No. :59320-77-3 MDL No. :MFCD00203855
Formula : C10H18O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 170.25 Pubchem ID :-
Synonyms :

Safety of [ 59320-77-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 59320-77-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 59320-77-3 ]

[ 59320-77-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 59320-77-3 ]
  • [ 498-00-0 ]
  • [ 205687-01-0 ]
YieldReaction ConditionsOperation in experiment
86.6% at 50℃; for 16h; 6 [Example 6] Synthesis of capsiate; trans-8-Methyl-6-nonenoic acid (1.00 g, 5.87 mmol) , vanillyl alcohol (1.085 g, 7.04 mmol) and Novozym 435 (100 mg) were measured and placed in a flask (25 ml) . The mixture in the flask free of a plug was heated with stirring in an oil bath at 50°C for 16 hrs. After 2 to 3 hrs of stirring with heating, attachment of water on the wall of the upper part of the flask was observed. The reaction mixture was returned to room temperature, hexane (25 ml) was added, and Novozym 435 and precipitated vanillyl alcohol were filtered off. Hexane (25 ml) was added to the filtrate, and the mixture was washed with 5% agueous citric acid solution (25 ml) and saturated brine (25 ml) , and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. Since production of polar impurity other than vanillyl alcohol was confirmed by TLC, the residue was dissolved in 50 ml of hexane and passed through a short column packed with 1.5 g of silica gel, and the silica gel was sufficiently washed away with a mixed solvent of hexane and ethyl acetate (volume ratio 10:1) . The above-mentioned impurity was not detected in the eluent by TLC. The eluent was concentrated under reduced pressure to give capsiate (1.56 g, yield 86.6%) as a colorless oil. This capsiate contained a trace amount of trans-8-methyl-6-nonenoic acid. EPO 1H-NMR (CDCl3, δ) : 0.95 (d, 6H, J=6.74Hz), 1.33-1.40 (m, 2H), 1.59-1.67 (m, 2H), 1.94-1.99 (m, 2H), 2.18-2.23 (m, IH), 2.33 (t, 2H, J=7.52Hz), 3.89 (s, 3H), 5.02 (s, 2H), 5.26-5.39 (m, 2H), 5.63 (br, IH), 6.83-6.90 (m, 3H)
51% With di-isopropyl azodicarboxylate; thiamine diphosphate In tetrahydrofuran at 20℃;
Reference： [1]Current Patent Assignee: AJINOMOTO COMPANY INC - WO2006/88239, 2006, A1 Location in patent: Page/Page column 40-41
[2]Appendino, Giovanni; Minassi, Alberto; Daddario, Nives; Bianchi, Federica; Tron, Gian Cesare [Organic Letters, 2002, vol. 4, # 22, p. 3839 - 3841]
  • 2
  • [ 59320-77-3 ]
  • [ 19408-84-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 2: diethyl ether / 72 h / Ambient temperature 3: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr
Reference： [1]Gannett, Peter M.; Nagel, Donald L.; Reilly, Pam J.; Lawson, Terence; Sharpe, Jody; Toth, Bela [Journal of Organic Chemistry, 1988, vol. 53, # 5, p. 1064 - 1071]
  • 3
  • [ 1196-92-5 ]
  • [ 59320-77-3 ]
  • [ 404-86-4 ]
YieldReaction ConditionsOperation in experiment
With lipase In tert-Amyl alcohol at 45℃; for 48h; Molecular sieve; Enzymatic reaction;
99.7 % With Novozym 435 In di-isopropyl ether at 69℃; Dean-Stark; 11; 15; 17; 22-25 Example 11: Preparation of capsaicin with excess amine in DIPE. At normal atmospheric pressure (approximately 1 atm), 8-methyl-6-nonenoic acid (3.65 g), vanillyl amine (1.1 equiv.), Novozym 435(tm) on beads (498.8 mg, 14 w/w% E/S) were refluxed (about 69 oC) in diisopropyl ether (45 mL) with a Dean-Stark trap to collect the generated water. After stirring at about 300 rpm overnight (19 h), the mixture was filtered to recover the lipase catalyst, and the filtrate was washed with 0.5 M aqueous HCl solution (10 mL). The aqueous phase was extracted with Et2O (10 mL×2) and the organic phase were combined, dried over anhydrous Na2SO4 and concentrated to give 6.53 g product ( % yield, very pale yellow color).
99.7 % With Novozym 435 In di-isopropyl ether at 69℃; Dean-Stark; Enzymatic reaction; 11; 15; 17; 18; 22-24 Example 11: Preparation of capsaicin with excess amine in DIPE. At normal atmospheric pressure (approximately 1 atm), 8-methyl-6-nonenoic acid (3.65 g), vanillyl amine (1.1 equiv.), Novozym 435(tm) on beads (498.8 mg, 14 w/w% E/S) were refluxed (about 69 oC) in diisopropyl ether (45 mL) with a Dean-Stark trap to collect the generated water. After stirring at about 300 rpm overnight (19 h), the mixture was filtered to recover the lipase catalyst, and the filtrate was washed with 0.5 M aqueous HCl solution (10 mL). The aqueous phase was extracted with Et2O (10 mL×2) and the organic phase were combined, dried over anhydrous Na2SO4 and concentrated to give 6.53 g product ( % yield, very pale yellow color).
Reference： [1]Anderson, Mattias; Afewerki, Samson; Berglund, Per; Cordova, Armando [Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 2113 - 2118]
[2]Current Patent Assignee: XP CHEMISTRIES - WO2022/229314, 2022, A1 Location in patent: Page/Page column 25-26; 28-31
[3]Current Patent Assignee: XP CHEMISTRIES - WO2022/229314, 2022, A1 Location in patent: Page/Page column 25; 26-27; 28; 29-30
  • 4
  • [ 59320-77-3 ]
  • [ 7149-10-2 ]
  • [ 404-86-4 ]
YieldReaction ConditionsOperation in experiment
75% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; Schlenk technique; 5.4 4.5.4 Capsaicin (1) A 100 mL round-bottom flask equipped with Schlenk adapter and stirring bar was charged with 750 mg (4.41 mmol, 1.0 eq.) 13 and 20 mL dry DMF were added. After cooling the reaction mixture to 0 °C, 1.83 mL (13.22 mmol, 3.0 eq.) Et3N, 1.7 g (5.29 mmol, 1.2 eq.) TBTU and 1.0 g (5.29 mmol, 1.2 eq.) vanillylamine hydrochloride were added successively. The yellowish suspension was stirred at RT for 2 h. The reaction mixture was quenched by the addition of 100 mL brine. A colorless precipitate formed which dissolved in water by the addition of water. The reaction solution was extracted with EtOAc (3 * 70 mL) and the combined organic layers were washed with 1 M HCl (1 * 50 mL), saturated NaHCO3-solution (1 * 50 mL), and brine (1 * 50 mL). The combined organic layers were dried over Na2SO4 and the solvent was evaporated under reduced pressure. The product was purified via flash chromatography (75 g silica gel, cyclohexane/EtOAc = 2/1, fraction size: 50 mL) yielding a sticky oil which crystallized under high vacuum and freezing in liquid nitrogen. (1.01 g, 75 %) m.p. = 58-61 °C. 1H NMR (300.36 MHz; CDCl3) δ = 6.80 (m, 3H), 5.70 (s, 2H), 5.30 (m, 2H), 4.34 (d, 3JHH = 5.5 Hz, 2H), 3.86 (s, 3H), 2.23 (m, 2H), 1.99 (m, 2H), 1.66 (m, 2H), 1.37 (m, 2H), 0.93 (d, 3JHH = 6.2 Hz, 6H) 13C NMR (75.53 MHz; CDCl3) δ = 173.0, 146.9, 145.3, 130.5, 138.2, 126.6, 120.9, 114.5, 110.8, 56.1, 43.7, 36.8, 32.4, 31.1, 29.4, 25.4, 22.8.
Reference： [1]Migglautsch, Anna K.; Willim, Melissa; Schweda, Bettina; Glieder, Anton; Breinbauer, Rolf; Winkler, Margit [Tetrahedron, 2018, vol. 74, # 43, p. 6199 - 6204]

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