7149-10-2

Basic information

• Product Name: 4-Hydroxy-3-methoxybenzylamine hydrochloride
• Synonyms: VANILLYLAMINE HCL;VANILLYLAMINE HYDROCHLORIDE;TIMTEC-BB SBB003667;N-VANILLYLAMINE HYDROCHLORIDE;4-HYDROXY-3-METHOXYBENZYLAMINE HCL;4-HYDROXY-3-METHOXYBENZYLAMINE HYDROCHLORIDE;4-AMINOMETHYL-2-METHOXYPHENOL HYDROCHLORIDE;4-Aminomethyl-2-methoxy-phenol Hydrochloride；
• CAS NO: 7149-10-2
• Molecular Formula: C₈H₁₁NO₂*ClH
• Molecular Weight: 189.64
• EINECS: 230-468-3
• Product Categories: Pharmaceutical Raw Materials;Chemical intermediate for Capsaicine;Anilines, Aromatic Amines and Nitro Compounds;Chemical Amines;Amines;Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Amines, Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 7149-10-2.mol

Chemical Properties

• Melting Point: 219-221 °C (dec.)(lit.)
• Boiling Point: 292.9 °C at 760 mmHg
• Flash Point: 130.9 °C
• Appearance: Off-white/Powder
• Vapor Pressure: 0.00102mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• Sensitive: Moisture Sensitive
• Stability: Hygroscopic
• BRN: 3915418
• CAS DataBase Reference: 4-Hydroxy-3-methoxybenzylamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-3-methoxybenzylamine hydrochloride(7149-10-2)
• EPA Substance Registry System: 4-Hydroxy-3-methoxybenzylamine hydrochloride(7149-10-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 7149-10-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 7149-10-2 differently. You can refer to the following data:
1. A metabolite of Capsaicin
2. A metabolite of Capsaicin.

InChI:InChI=1/C8H11NO2/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,10H,5,9H2,1H3/p+1

Synthetic route

vanillin oxime (2874-33-1) → vanillylamine hydrochloride (7149-10-2)

Conditions	Yield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 3h;	100%
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 4h;	98%
Stage #1: vanillin oxime With hydrogen In ethanol at 40℃; for 8h; Stage #2: With hydrogenchloride In ethanol; water pH=1; Temperature;	90.5%

vanillin (121-33-5) → vanillylamine hydrochloride (7149-10-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / 6 h / 20 °C 2: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 760.05 Torr View Scheme
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / 6 h / 20 °C 2: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 760.05 Torr View Scheme
Stage #1: vanillin With ammonia In methanol at 20℃; for 3h; Stage #2: With methanol; sodium tetrahydroborate at 45℃; Stage #3: With hydrogenchloride In water at 0℃; for 3h; Temperature; Concentration;	112 g
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate trihydrate / water / 2 h / 80 °C 2: palladium 10% on activated carbon; hydrogenchloride; hydrogen / ethanol / 24 h / 20 °C / 760.05 Torr View Scheme

(E)-4-hydroxy-3-methoxybenzaldehyde oxime (134283-49-1) → vanillylamine hydrochloride (7149-10-2)

Conditions	Yield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr; for 24h;	74%

4-hydroxy-3-methoxybenzaldehyde O-methyloxime (93249-67-3) → vanillylamine hydrochloride (7149-10-2)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 4h;

vanillin (121-33-5) + KOH-solution → vanillylamine hydrochloride (7149-10-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / pyridine / Ambient temperature 2: H2, conc. hydrochloric acid / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme
Multi-step reaction with 2 steps 1: 83 percent / NH2OH*HCl, pyridine / ethanol / 24 h / Ambient temperature 2: 98 percent / H2, conc. hydrochloric acid / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

Upstream product

• 134283-49-1 (E)-4-hydroxy-3-methoxybenzaldehyde oxime 
• 121-33-5 vanillin 
• 93249-67-3 4-hydroxy-3-methoxybenzaldehyde O-methyloxime 
• 2874-33-1 vanillin oxime 

Downstream Products

• 89575-10-0 N-heptanoate vanillylamide 
• 184003-09-6 1-[(E)-2-(4-Chloro-phenyl)-vinyl]-3-(4-hydroxy-3-methoxy-benzyl)-thiourea 
• 121-33-5 vanillin 
• 849343-53-9 12-phenylacetylrinvanil 
• 457643-60-6 Rinvanil 
• 96513-74-5 N-vanillyl-9-octadecynamide 
• 58493-49-5 olvanil 
• 35103-38-9 4-acetoxy-N-acetyl-3-methoxy-benzylamine 
• 209737-39-3 [1S-(1α,2β,3β,4α)]-4-[7-(Butylamino)-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-2,3-dihydroxy-N-[(4-hydroxy-3-methoxyphenyl)-methyl]-cyclopentanecarboxamide 
• 51749-22-5 (4-hydroxy-3-methoxybenzyl)urea 

Relevant articles and documents

Fabrication of ω-Transaminase@Metal-Organic Framework Biocomposites for Efficiently Synthesizing Benzylamines and Pyridylmethylamines

In this study, ten ω-transaminases (ω-TAs) have been investigated to efficiently catalyze the synthesis of twenty-four functionalized benzylamines and pyridylmethylamines. We optimized the reactions, screened suitable amino donors and compared ω-transaminases activities for all aromatic aldehyde substrates. Under the optimized conditions, eighteen aromatic amines have been obtained with 60.4%–96.6% conversions and isolated only via simple extraction and recrystallization with 18.5%–81% yields on a preparative scale. Furthermore, we first immobilized the Bm-STA onto the MOFs via the physical adsorption to overcome the limitation of free enzyme and improve their industrial applications. The obtained Bm-STA/UiO-66-NH2 composites exhibited not only high enzymes loading (80.4 mg g?1) and enzyme activity recovery (95.8%), but also the better reusability, storage stability, pH stability and the tolerance to acetone and DMF.

Efficient hydrogenation of benzaldoximes and Schiff bases on ceramic high-porosity palladium catalysts

An efficient catalytic method for the synthesis of benzyl- and dibenzylamines by hydrogenating oximes and Schiffbases was developed on palladium supported high-porosity foamed ceramic block catalyst. The multiple regeneration ability of the foamed ceramic block catalyst can significantly decrease the Pd consumption as compared to the use of the conventional 10%Pd/C catalyst. Owing to a high hardness of the foamed ceramic catalyst, the reaction mixture can rapidly be removed from the reactor without using filtering devices. The structures produced by the reaction are fragments of biologically active and natural molecules. Antiproliferative properties of dibenzylamines revealed on the sea urchin embryo model suggest that these compounds can be considered as promising agents for the design of new anticancer drugs.

Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists

The transient receptor potential vanilloid type-2 (TRPV2) protein is a nonselective Ca2+ permeable channel member of the TRPV subfamily, still considered an orphan TRP channel due to the scarcity of available selective and potent pharmacological tools and endogenous modulators. Here we describe the discovery of novel synthetic long-chain capsaicin derivatives as potent TRPV2 antagonists in comparison to the totally inactive capsaicin, the role of their hydrophobic chain, and how the structure-activity relationships of such derivatives led, through a ligand-based approach, to the identification of endogenous long-chain fatty acid ethanolamides or primary amides acting as TRPV2 antagonists. Both synthetic and endogenous antagonists exhibited differential inhibition against known TRPV2 agonists characterized by distinct kinetic profiles. These findings represent the first example of both synthetic and naturally occurring TRPV2 modulators with efficacy in the submicromolar/low-micromolar range, which will be useful for clarifying the physiopathological roles of this receptor, its regulation, and its targeting in pathological conditions.

Preparation method for vanillylamine hydrochloride

The invention discloses a preparation method for vanillylamine hydrochloride. The preparation method comprises the following steps: adding 3-methoxy-4-hydroxybenzaldehyde oxime into a reaction container, then adding alcohol and a composite catalyst, introducing hydrogen under a normal pressure condition for protection and carrying out heating for a reaction; and carrying out filtering after the reaction, adding hydrochloric acid with mass percentage concentration of 30% into a filtrate, adjusting the pH value of the filtrate to 1, filtering out a precipitated white crystal and carrying out vacuum drying so as to obtain finished vanillylamine hydrochloride. The method provided by the invention is simple in operation process, low in cost, high in yield, low in reaction conditions, high in product purity and environment-friendly. The method can overcome the disadvantages that a direct reduction and amination method for production of vanillylamine hydrochloride from ammonium formate has low yield, usage of a high-pressure reaction leads to great danger, usage of precious metals as catalysts results in high investment and the like in the prior art.

A capsaicin preparation method

The invention discloses a preparation method of capsaicine. The method takes vanillin as a raw material, and comprises the steps of: carrying out reaction in an ammonia-gas-containing methanol solution; carrying out hydrogenation reduction by sodium borohydride; carrying out hydrochlorination on the vanillin amine collected from the reaction product; adding the intermediate vanillin amine hydrochloride into a dimethyl formamide (DMF) solvent, and dissolving; and adding nonoic acid, triethylamine and a condensing agent HBTU into the solution, and carrying out condensation reaction to obtain the target product capsaicine. The detection proves that the purity reaches up to more than 98%, and the total yield is 72.1%-81.1%. The preparation method is mild in reaction conditions, high in controllability of the operation process, low in cost and good in purity; a thin layer chromatography (TLC) detection method is used for controlling the reaction process, so that the obtained target product capsaicine is stable in quality and suitable for industrial production.

APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT

PROBLEM TO BE SOLVED: To prepare analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. SOLUTION: The present invention relates to an N6-substituted adenosine derivative and an N6-substituted adenine derivative selected from the group consisting of specific compounds. The present invention also relates to a pharmaceutical composition at least comprising a therapeutically effective amount of the compounds and a pharmaceutically acceptable carrier. The invention further relates to the compounds used in preparation of analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. COPYRIGHT: (C)2016,JPO&INPIT

N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF

The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.

N6-SUBSTITUTED ADENOSINE DERIVATIVES, N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF

The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.

Facile synthesis and promising antibacterial properties of a new guaiacol-based polymer

A new acrylamide-type monomer (N-(4-hydroxy-3-methoxy-benzyl)-acrylamide) derived from guaiacol was successfully synthesized. Polymers containing guaiacol moiety were obtained via conventional radical polymerization of this monomer with AIBN as initiator. The influence of reaction time, initiator concentration and temperature on polymers characteristics was studied. Evaluation of the termination mode in free-radical polymerization was performed by MALDI-TOF mass spectrometry. Termination occurs mainly by disproportionation reaction. Additional peaks in the spectrum were attributed to side chain reactions implying phenoxy radicals. This new polymer exhibits a potential antibacterial activity against Bacillus subtilis by using anti-adhesion and anti-biofilm tests. After an adhesion time of 3 h, compared to a non-coated glass slide, there was a decrease of bacteria of 99% on the polymer coated glass slide. After three days of culture in a bacterial suspension, no biofilm was observed on the polymer coated surface.

Method for producing vanillylamine hydrochloride

The invention relates to a method for producing vanillylamine or one of the salts thereof, whereby a) vanillin is reacted with hydroxylamine or the salts of the same in the presence of an organic salt which can optionally be produced in situ; and b) the vanillyloxime produced is then hydrogenated with hydrogen in the presence of a suitable catalyst and an organic and/or inorganic acid. Said method is characterised in that step a) is carried out in an inorganic or organic acid used as a diluent.