2-Methoxybenzoic acid (O-Methylsalicylic acid; NSC 3778) is a novel antiemetic that is also widely used as an internal standard of salicylic acid and its putative biosynthetic precursors in cucumber leaves. Another known use is in the synthesis of Benextramine. 2-Methoxybenzoic acid is also a novel antiemetic which prevents nausea and vomiting in humans. Its actions are unclear but most likely involves the chemoreceptor trigger zone (CTZ)

Physicochemical Properties

Molecular Formula	C8H8O3
Molecular Weight	152.1473
Exact Mass	152.047
CAS #	579-75-9
Related CAS #	2-Methoxybenzoic acid-13C6
PubChem CID	11370
Appearance	White to off-white solid powder
Density	1.2±0.1 g/cm3
Boiling Point	279.9±13.0 °C at 760 mmHg
Melting Point	98-100 °C(lit.)
Flash Point	116.3±13.3 °C
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.546
LogP	1.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Heavy Atom Count	11
Complexity	144
Defined Atom Stereocenter Count	0
InChi Key	ILUJQPXNXACGAN-UHFFFAOYSA-N
InChi Code	InChI=1S/C8H8O3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5H,1H3,(H,9,10)
Chemical Name	Benzoic acid, 2-methoxy-
Synonyms	O-Methylsalicylic acid; NSC 3778; NSC-3778; NSC3778; Salicylic acid methyl ether
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References	[1]. Ortho-anisic acid as internal standard for the simultaneous quantitation of salicylic acid and its putative biosynthetic precursors in cucumber leaves. Anal Biochem. 1993 Nov 1;214(2):500-5.
Additional Infomation	O-methylsalicylic acid is a methoxybenzoic acid that is the methyl ether of salicylic acid. It has a role as a non-steroidal anti-inflammatory drug and a flavouring agent. It is a conjugate acid of an O-methylsalicylate. 2-Methoxybenzoic acid has been reported in Desmos chinensis, Origanum minutiflorum, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~657.25 mM)

Solubility (In Vivo)

Solubility in Formulation 1: 2.5 mg/mL (16.43 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (16.43 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (16.43 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	6.5725 mL	32.8623 mL	65.7246 mL
	5 mM	1.3145 mL	6.5725 mL	13.1449 mL
	10 mM	0.6572 mL	3.2862 mL	6.5725 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.