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Salicylhydroxamic acid

Salicylhydroxamic acid structure

CAS No:
89-73-6
Formula:
C7H7NO3
Chemical Name:
Salicylhydroxamic acid
Synonyms:
Benzamide,N,2-dihydroxy-;Salicylohydroxamic acid;N,2-Dihydroxybenzamide;2-Hydroxybenzohydroxamic acid;SHA;o-Hydroxybenzohydroxamic acid;2-Hydroxyphenylhydroxamic acid;SHAM;N-Salicylhydroxamic acid;2-Hydroxybenzenehydroxamic acid;Salicylhydroxamic acid;NSC 193440;NSC 5088;1-N-Hydroxy2-hydroxybenzene-1-carboximidic acid;1953-59-9;72027-50-0
Categories:
Cosmetic Ingredient > Skin Conditioning

Description

off-white powder

Salicylhydroxamic acid is a hydroxamic acid that is N-hydroxybenzamide carrying a phenolic hydroxy group at position 2. It has a role as an antibacterial drug, a trypanocidal drug, an EC 3.5.1.5 (urease) inhibitor and an EC 1.11.2.2 (myeloperoxidase) inhibitor. It is a member of phenols and a hydroxamic acid.

Salicylhydroxamic acid Basic Attributes

Molecular Weight：

153.14

Exact Mass：

153.14

EC Number：

201-934-3

UNII：

8Q07182D0T

NSC Number：

193440|5088

DSSTox ID：

DTXSID5075365

HScode：

2924299090

Characteristics

PSA：

69.6

XLogP3：

0.9

Appearance：

brownish crystalline powder

Density：

1.4±0.1 g/cm3

Melting Point：

168 °C

Flash Point：

248.9ºC

Refractive Index：

1.626

Water Solubility：

It is soluble in water.

Storage Conditions：

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R40

safety instructions：

S22-S26-S36-S24/25

RTECS Number：

VO6870000

Marks：

Xn:Harmful;

Stability/Shelf Life：

Stable. Incompatible with strong bases, strong oxidizing agents. Combustible.

Precautionary statement(s)：

P261-P280-P305 + P351 + P338

Hazard Statements：

H312-H315-H319-H332-H335-H351

GHS Classification：

|Warning|H312 (95.49%): Harmful in contact with skin [Warning Acute toxicity, dermal]|P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 133 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA. (See all compounds classified as Trypanocidal Agents.)|Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)|Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

MeSH Entry Terms：

salicylhydroxamate

Salicylhydroxamic acid Use and Manufacturing

Methods of Manufacturing

General procedure: To an aqueous solution of AgNO3 (1.7 mg, 0.01 mmol, 1 molpercent) in water (6 mL), vitamin K3 (2.6 mg, 0.015 mmol, 1.5 molpercent) dissolved in ethanol (2 mL) wasadded, and then an appropriate aldehyde (1 mmol) dissolved in THF (2 mL) wasadded to the reaction mixture followed by the addition of NH2OHHCl (69 mg, 1 mmol) and Et3N (0.14 mL, 1 mmol). The final solvent ratio (H2O:EtOH:THF)was (3:1:1). The mixture was stirred at room temperature for 30 min under visiblelight irradiation using a halogen lamp (HALOPAR 20 75 W 230 V 30-GU10;Osram, Italy). The reaction was monitored by TLC. After completion of thereaction, EtOAc (30 mL) was added. The aqueous layer was collected andconcentrated under reduced pressure at 25 C to obtain pure sample containing Agnanoparticles that was characterized by UV–Vis and TEM analyses. The organicphase was collected, dried over anhydrous MgSO4 and filtered. The solvent wasevaporated under vacuum using a rotatory evaporator and then the residue was purified by a short plug of silica gel using (Hexane:EtOAc, 1:1) to obtainhydroxamic acids 2a–j in 81–92percent yield.A solution of hydroxylamine (3M) was stirred at RT under N2-atmosphere, then NaOH (7.05 mol in 240 ml H2O) and methyl salicylate (300 g in 750 ml dioxane) were added dropwise and the reaction mixture was stirred for 12 hours at RT. After completion, the reaction solvent was evaporated at 50°C, the remaining residue cooled and acidified with 12N HCI. The mixture was stirred for 30 min. at 10-15°C and the resulting precipitate filtrated, washed with ice-water and dried under reduced pressure at 90 °C. Ouantitative Yielding 2-Hvdroxybenzhvdroxamic Acid (intermediate 1).

Uses

Complexing agent.

Computed Properties

Molecular Weight:153.14
XLogP3:0.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:153.042593085
Monoisotopic Mass:153.042593085
Topological Polar Surface Area:69.6
Heavy Atom Count:11
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of Salicylhydroxamic acid

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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Salicylhydroxamic acid

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