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2-Hydroxybenzylamine

2-Hydroxybenzylamine structure

CAS No:
932-30-9
Formula:
C7H9NO
Chemical Name:
2-Hydroxybenzylamine
Synonyms:
2-(3-CHLOROPHENOXY)MALONDIALDEHYDE;2-HYDROXYBENZYLAMINE[2-(AMINOMETHYL)PHENOL];Phenol, 2-(aminomethyl)-;2-Hydroxybenzylamine;2-Hydroxybenzylamine, (2-Hydroxyphenyl)methylamine;2-HydroxybenzylaMine, 98% 1GR;2-HydroxybenzeneMethanaMine;NSC 127870
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

Description

white to light yellow crystal powde

2-(aminomethyl)phenol is under investigation in clinical trial NCT03556319 (2-HOBA: Multiple Dosing Study in Older Adults).

2-Hydroxybenzylamine (2-HOBA), also known as salicylamide, is a potent γKA scavenger that scavenges γKAs 980-fold faster than the formation of γKA protein adducts and therefore protects cells from the deleterious effects of γKA adducts. 2-HOBA is currently being developed as a nutritional supplement to help protect against the development of conditions associated with dicarbonyl electrophile formation, such as the cognitive decline observed with Mild Cognitive Impairment or Alzheimer's disease.

2-Hydroxybenzylamine Basic Attributes

Molecular Weight：

123.15

Exact Mass：

123.15

EC Number：

213-249-7

UNII：

696R5N4NRM

NSC Number：

127870

Color/Form：

Beige to Brown

HScode：

29222990

Characteristics

PSA：

46.2

XLogP3：

0.5

Density：

1.141±0.06 g/cm3(Predicted)

Melting Point：

127 °C

Boiling Point：

245.0±15.0 °C(Predicted)

Flash Point：

102.0±20.4 °C

Refractive Index：

1.594

PKA：

8.63±0.35(Predicted)

Critical Temperature & Pressure：

under inert gas (nitrogen or Argon) at 2–8 °C

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

26-37/39

Marks：

Hazard note：

Irritant

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

36/37/38

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 42 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

2-(aminomethyl)phenol

2-Hydroxybenzylamine Use and Manufacturing

Uses

A potent γ-ketoaldehyde scavenger that has been shown to protects cardiac sodium channel (NaV1.5) from oxidant-induced inactivation

Production

A simplified method for extracting 2-hydroxybenzylamine from buckwheat is as follows:1. Dry the roots, stems, and seeds of buckwheat separately. Grind them into a powder using liquid nitrogen.2. Mix the powder with deionized water and adjust the pH of the solution to 5.0. Add an enzyme mixture consisting of cellulase and pectinase, with a weight ratio of 2:1 to the powder. Perform enzymatic hydrolysis at a temperature of 25°C for 40 minutes. Filter the mixture after hydrolysis.3. Mix the filter residue obtained in step 2 with 95% ethanol using a solid-liquid ratio of 1g:10mL. Perform ultrasonic extraction at an ultrasound power density of 100W/cm2, ultrasound frequency of 30kHz, extraction temperature of 20°C, and extraction time of 30 minutes. Repeat the extraction process three times, filter the extracts, and combine them.4. Concentrate the supernatant obtained in step 3 under reduced pressure to obtain a Chemicalbook extract. Add a 3 wt% sodium hydroxide solution to dissolve the extract. Filter the solution to obtain the filtrate.5. Adjust the filtrate obtained in step 4 to pH 3 using hydrochloric acid, resulting in an adjusted solution. Pass the adjusted solution through an NDA-150 resin column at a temperature of 20°C and a flow rate of 10 BV/h until saturated adsorption is achieved.6. After reaching saturated adsorption, elute the filtrate obtained in step 4 with an 8 wt% sodium hydroxide solution at 50°C and a flow rate of 2 BV/h. Collect twice the volume of the column volume. Then, elute the filtrate obtained in step 5 with a 3 wt% sodium hydroxide solution at 50°C and a flow rate of 2 BV/h. Collect once the volume of the column volume. Lastly, elute the filtrate obtained in step 5 with water at 60°C and a flow rate of 3 BV/h. Collect once the volume of the column volume. Combine the three eluents.7. Concentrate the combined eluents under reduced pressure and recrystallize them using edible alcohol. Separate the crystals to obtain 2-hydroxybenzylamine.

Computed Properties

Molecular Weight:123.15
XLogP3:0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:123.068413911
Monoisotopic Mass:123.068413911
Topological Polar Surface Area:46.2
Heavy Atom Count:9
Complexity:85
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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