Vanillylamine HCl
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MedKoo CAT#: 464304

CAS#: 7149-10-2 (HCl)

Description: Vanillylamine is a chemical compound that is an intermediate in the biosynthesis of capsaicin. Vanillylamine is produced from vanillin by the enzyme vanillin aminotransferase. It is then converted with 8-methyl-6-nonenoic acid into capsaicin by the enzyme capsaicin synthase.

Chemical Structure

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Vanillylamine HCl
CAS# 7149-10-2 (HCl)
Instruction

Theoretical Analysis

MedKoo Cat#: 464304
Name: Vanillylamine HCl
CAS#: 7149-10-2 (HCl)
Chemical Formula: C8H12ClNO2
Exact Mass: 189.06
Molecular Weight: 189.639
Elemental Analysis: C, 50.67; H, 6.38; Cl, 18.69; N, 7.39; O, 16.87

Price and Availability

Size Price Availability Quantity
1g USD 250 2 Weeks
5g USD 550 2 Weeks
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Synonym: Vanillylamine HCl; Vanillylamine hydrochloride; NSC 62020; NSC62020; NSC-62020;

IUPAC/Chemical Name: 4-(aminomethyl)-2-methoxyphenol hydrochloride

InChi Key: PUDMGOSXPCMUJZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H11NO2.ClH/c1-11-8-4-6(5-9)2-3-7(8)10;/h2-4,10H,5,9H2,1H3;1H

SMILES Code: COc1c(O)ccc(CN)c1.Cl

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 189.64 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Manfrão-Netto JHC, Lund F, Muratovska N, Larsson EM, Parachin NS, Carlquist M. Metabolic engineering of Pseudomonas putida for production of vanillylamine from lignin-derived substrates. Microb Biotechnol. 2021 Feb 3. doi: 10.1111/1751-7915.13764. Epub ahead of print. PMID: 33533574.

2: Forcados GE, Sallau AB, Muhammad A, Erukainure OL, James DB. Vitex doniana Leaves Extract Ameliorates Alterations Associated with 7, 12-Dimethyl Benz[a]Anthracene-Induced Mammary Damage in Female Wistar Rats. Nutr Cancer. 2021;73(1):98-112. doi: 10.1080/01635581.2020.1743866. Epub 2020 Mar 28. PMID: 32223342.

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6: Liu Y, Afanasenko A, Elangovan S, Sun Z, Barta K. Primary Benzylamines by Efficient N-Alkylation of Benzyl Alcohols Using Commercial Ni Catalysts and Easy-to-Handle Ammonia Sources. ACS Sustain Chem Eng. 2019 Jul 1;7(13):11267-11274. doi: 10.1021/acssuschemeng.9b00619. Epub 2019 May 31. PMID: 31304071; PMCID: PMC6614922.

7: Leporini M, Loizzo MR, Tundis R, La Torre C, Fazio A, Plastina P. Non-Pungent n-3 Polyunsaturated Fatty Acid (PUFA)-Derived Capsaicin Analogues as Potential Functional Ingredients with Antioxidant and Carbohydrate-Hydrolysing Enzyme Inhibitory Activities. Antioxidants (Basel). 2019 Jun 5;8(6):162. doi: 10.3390/antiox8060162. PMID: 31195742; PMCID: PMC6616483.

8: Cione E, Plastina P, Pingitore A, Perri M, Caroleo MC, Fazio A, Witkamp R, Meijerink J. Capsaicin Analogues Derived from n-3 Polyunsaturated Fatty Acids (PUFAs) Reduce Inflammatory Activity of Macrophages and Stimulate Insulin Secretion by β-Cells In Vitro. Nutrients. 2019 Apr 24;11(4):915. doi: 10.3390/nu11040915. PMID: 31022842; PMCID: PMC6520993.

9: Arce-Rodríguez ML, Ochoa-Alejo N. Biochemistry and molecular biology of capsaicinoid biosynthesis: recent advances and perspectives. Plant Cell Rep. 2019 Sep;38(9):1017-1030. doi: 10.1007/s00299-019-02406-0. Epub 2019 Apr 2. PMID: 30941502.

10: Arce-Rodríguez ML, Ochoa-Alejo N. An R2R3-MYB Transcription Factor Regulates Capsaicinoid Biosynthesis. Plant Physiol. 2017 Jul;174(3):1359-1370. doi: 10.1104/pp.17.00506. Epub 2017 May 8. PMID: 28483879; PMCID: PMC5490919.

11: Ogawa K, Murota K, Shimura H, Furuya M, Togawa Y, Matsumura T, Masuta C. Evidence of capsaicin synthase activity of the Pun1-encoded protein and its role as a determinant of capsaicinoid accumulation in pepper. BMC Plant Biol. 2015 Mar 28;15:93. doi: 10.1186/s12870-015-0476-7. PMID: 25884984; PMCID: PMC4386094.

12: Kobata K, Takemura I, Tago G, Moriya T, Kubota K, Nakatani S, Wada M, Watanabe T. Formation of long-chain N-vanillyl-acylamides from plant oils. Biosci Biotechnol Biochem. 2014;78(7):1242-5. doi: 10.1080/09168451.2014.912118. Epub 2014 May 28. PMID: 25229865.

13: Shimada C, Uesawa Y, Ishihara M, Kagaya H, Kanamoto T, Terakubo S, Nakashima H, Takao K, Saito T, Sugita Y, Sakagami H. Quantitative structure-cytotoxicity relationship of phenylpropanoid amides. Anticancer Res. 2014 Jul;34(7):3543-8. PMID: 24982367.

14: Weber N, Ismail A, Gorwa-Grauslund M, Carlquist M. Biocatalytic potential of vanillin aminotransferase from Capsicum chinense. BMC Biotechnol. 2014 Apr 9;14:25. doi: 10.1186/1472-6750-14-25. PMID: 24712445; PMCID: PMC4000252.

15: Kobata K, Sugawara M, Mimura M, Yazawa S, Watanabe T. Potent production of capsaicinoids and capsinoids by Capsicum peppers. J Agric Food Chem. 2013 Nov 20;61(46):11127-32. doi: 10.1021/jf403553w. Epub 2013 Nov 6. PMID: 24147886.

16: Tomohiro D, Mizuta K, Fujita T, Nishikubo Y, Kumamoto E. Inhibition by capsaicin and its related vanilloids of compound action potentials in frog sciatic nerves. Life Sci. 2013 Mar 14;92(6-7):368-78. doi: 10.1016/j.lfs.2013.01.011. Epub 2013 Jan 24. PMID: 23352977.

17: Gururaj HB, Padma MN, Giridhar P, Ravishankar GA. Functional validation of Capsicum frutescens aminotransferase gene involved in vanillylamine biosynthesis using Agrobacterium mediated genetic transformation studies in Nicotiana tabacum and Capsicum frutescens calli cultures. Plant Sci. 2012 Oct;195:96-105. doi: 10.1016/j.plantsci.2012.06.014. Epub 2012 Jul 2. PMID: 22921003.

18: Kobata K, Mimura M, Sugawara M, Watanabe T. Synthesis of stable isotope- labeled precursors for the biosyntheses of capsaicinoids, capsinoids, and capsiconinoids. Biosci Biotechnol Biochem. 2011;75(8):1611-4. doi: 10.1271/bbb.110187. Epub 2011 Aug 7. PMID: 21821932.

19: Lang Y, Kisaka H, Sugiyama R, Nomura K, Morita A, Watanabe T, Tanaka Y, Yazawa S, Miwa T. Functional loss of pAMT results in biosynthesis of capsinoids, capsaicinoid analogs, in Capsicum annuum cv. CH-19 Sweet. Plant J. 2009 Sep;59(6):953-61. doi: 10.1111/j.1365-313X.2009.03921.x. Epub 2009 May 18. PMID: 19473323.

20: Chanda S, Bashir M, Babbar S, Koganti A, Bley K. In vitro hepatic and skin metabolism of capsaicin. Drug Metab Dispos. 2008 Apr;36(4):670-5. doi: 10.1124/dmd.107.019240. Epub 2008 Jan 7. PMID: 18180272.