N-1-Naphthylphthalamic acid is a polar auxin transport inhibitor. N-1-Naphthylphthalamic acid disrupts maize leaf initiation, KNOX protein regulation, and leaf margin formation.

Physicochemical Properties

Molecular Formula	C18H13NO3
Molecular Weight	291.31
Exact Mass	291.09
CAS #	132-66-1
Related CAS #	132-67-2 (hydrochloride salt)
PubChem CID	8594
Appearance	White to off-white solid powder
Density	1.355g/cm3
Boiling Point	450.8ºC at 760mmHg
Melting Point	185-190 °C
Flash Point	226.4ºC
Vapour Pressure	6.51E-09mmHg at 25°C
LogP	3.863
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Heavy Atom Count	22
Complexity	423
Defined Atom Stereocenter Count	0
InChi Key	JXTHEWSKYLZVJC-UHFFFAOYSA-N
InChi Code	InChI=1S/C18H13NO3/c20-17(14-9-3-4-10-15(14)18(21)22)19-16-11-5-7-12-6-1-2-8-13(12)16/h1-11H,(H,19,20)(H,21,22)
Chemical Name	2-(naphthalen-1-ylcarbamoyl)benzoic acid
Synonyms	NSC 204421 NSC-204421 NSC204421
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]. Physical and chemical properties of cow cockle seeds (Vaccaria hispanica (Mill.) Rauschert) genetic resources of Turkey. [2]. The action of specific inhibitors of auxin transport on uptake of auxin and binding of N-1-naphthylphthalamic acid to a membrane site in maize coleoptiles. Planta. 1981 May;152(1):13-8.
Additional Infomation	Naptalam is a dicarboxylic acid monoamide which results from addition of one equivalent of 1-naphthylamine to phthalic anhydride. It has a role as a herbicide. It is a dicarboxylic acid monoamide, a carboxylic acid and a N-(1-naphthyl)carboxamide. It is a conjugate acid of a naptalamate. See also: Naptalam-sodium (annotation moved to).

Solubility Data

Solubility (In Vitro)

DMSO : ~33.33 mg/mL (~114.42 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.58 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 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 (8.58 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	3.4328 mL	17.1638 mL	34.3277 mL
	5 mM	0.6866 mL	3.4328 mL	6.8655 mL
	10 mM	0.3433 mL	1.7164 mL	3.4328 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.