Dihydrocapsaicin

• CAS: 19408-84-5
• Catalog Number: ACM19408845-1
• Category: Inhibitors
• Molecular Weight: 307.43
• Molecular Formula: C18H29NO3
• Description: Dihydrocapsaicin, a capsaicin, is a potent and selective TRPV1 (transient receptor potential vanilloid channel 1) agonist. Dihydrocapsaicin reduces AIF, Bax, and Caspase-3 expressions, and increased Bcl-2, Bcl-xL and p-Akt levels. Dihydrocapsaicin enhances the hypothermia-induced neuroprotection following ischemic stroke via PI3K/Akt regulation in rat.
• Synonyms: N-(4-Hydroxy-3-methoxybenzyl)
• IUPAC Name: N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide
• Canonical SMILES: CC(C)CCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• InChI: InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)
• InChI Key: XJQPQKLURWNAAH-UHFFFAOYSA-N
• Boiling Point: 497.4±35.0 °C
• Melting Point: 62-65 °C (lit.)
• Density: 1.026±0.06 g/ml
• Appearance: White powder
• pKa: 9.76±0.20

Synthetic Use

Upstream Synthesis Route 1

• 1196-92-5
• 205651-88-3

• 19408-84-5

Reference: [1]Kaga, Harumi; Miura, Masakatsu; Orito, Kazuhiko
[Synthesis, 1989, # 11, p. 864 - 866]

Upstream Synthesis Route 2

• 404-86-4

• 19408-84-5

Reference: [1]Gallou, Fabrice; Gao, Eugene S.; Lipshutz, Bruce H.; Takale, Balaram S.; Thakore, Ruchita R.
[Green Chemistry, 2020, vol. 22, # 18, p. 6055 - 6061]
[2]Current Patent Assignee: SHANGHAI ALADDIN BIOCHEMICAL TECH - CN105418445, 2016, A
Location in patent: Paragraph 0018; 0019; 0020
[3]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]

Upstream Synthesis Route 3

• 25775-90-0

• 19408-84-5

Reference: [1]Journal of Organic Chemistry,1988,vol. 53,p. 1064 - 1071