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Naphthalene Acetic Acid is a synthetic plant hormone belonging to the auxin family.
Naphthalene Acetic Acid is widely used in commercial rooting products, agriculture, and plant tissue culture to stimulate the growth of adventitious and lateral roots in stem and leaf cuttings.
Naphthalene Acetic Acid is an organic compound with the formula C10H7CH2CO2H and it is colorless solid is soluble in organic solvents.
CAS Number: 81872-10-8
Molecular Formula: C22H23NO4S2
Molecular Weight: 429.55
EINECS Number: 201-705-8
Synonyms: Gossypol acetic acid, Gossypol acetate, Gossypol-Acetic acid, Acetate gossypol, Acetate-gossypol, Gossypol (acetic acid), Gossypol acetic acid salt, Gossypol AcOH salt, GossypolAcOHSalt, (+/−)-Gossypol acetic acid, (R)-Gossypol acetic acid, (S)-Gossypol acetic acid, (-)-Gossypol acetic acid, (R)-(-)-Gossypol acetic acid, R-(-)-gossypol acetic acid, Gossypol acetic acid, R-, Gossypol acetic acid, (S)-, AT-101, AT101, BL-193, NSC-19048, NSC-727858, CAS 12542-36-8, CAS 5453-04-3, CAS 115038-46-5, CAS 732279-26-4, UNII:U9GNI6VT5N, DTXSID901059687, DTXSID90921593, RefChem:782656, C32H34O10, Gossypol acetic acid clathrate, 1-NAPHTHYLACETICACIDα-NAPHTHYLACETICACID;1-[(S)-3-(Benzoylthio)-2-methyl-1-oxopropyl]-4α-(phenylthio)-L-proline;S-Benzoyl-4-phenylthiocaptopril;(4S)-N-[3-(Benzoylsulfanyl)-2(S)-methylpropionyl]-4-(phenylsulfanyl)-L-proline;Zofenopril;NAA(R);NAA(TM);RARECHEM AL BO 0198
Naphthalene Acetic Acid features a carboxylmethyl group (CH2CO2H) linked to the "1-position" of naphthalene.
Naphthalene Acetic Acid is a synthetic plant growth regulator belonging to the auxin class of hormones.
It is widely used in agriculture and horticulture to control plant growth processes such as root formation, fruit development, flowering, and fruit drop regulation.
Naphthalene Acetic Acid is mainly used to stimulate rooting and manage fruit retention or thinning, making it an important tool in crop production and plant propagation.
This improves yield control and plant production efficiency.
Naphthalene Acetic Acid is a naphthalene derivative with an acetic acid functional group, giving it strong auxin-like activity in plants.
Naphthalene Acetic Acid binds to plant auxin signaling systems and influences gene expression related to growth and development.
This improves regulation of plant physiological processes.
Naphthalene Acetic Acid appears as a white to off-white crystalline solid, with low solubility in water but better solubility in organic solvents or as salt forms (such as sodium NAA).
This improves formulation flexibility in agricultural products.
Functionally, it acts as a rooting agent, fruit thinning regulator, anti-fruit drop agent, and general plant growth regulator.
Its stability makes it effective at low concentrations over a wide range of crops.
This improves agricultural efficiency and consistency.
Naphthalene Acetic Acid is best described as a synthetic auxin used to regulate plant growth, enhance rooting, and control fruit development in agriculture and horticulture.
Naphthalene Acetic Acid is especially important because it acts as a synthetic, highly stable auxin signal that can override or reinforce natural plant hormone balance.
Naphthalene Acetic Acid makes it useful for deliberately controlling plant development rather than just supporting it.
This improves precision in agricultural regulation.
Naphthalene Acetic Acid interacts with the auxin receptor pathway (TIR1/AFB complex), leading to degradation of repressor proteins and activation of auxin-responsive genes.
Naphthalene Acetic Acid triggers downstream changes in growth, cell division, and differentiation.
This improves understanding of plant hormone signaling.
Naphthalene Acetic Acid influences proton pump activity in cell membranes, promoting cell wall loosening and expansion under turgor pressure.
This is part of the classic auxin “acid growth” response.
Naphthalene Acetic Acid improves mechanistic insight into plant growth.
In fruit abscission regulation, Naphthalene Acetic Acid is particularly effective at modifying the abscission zone at the base of fruit stems.
It can delay or prevent fruit drop by maintaining hormonal signals that keep cells attached.
Naphthalene Acetic Acid improves harvest retention and crop yield.
In selective thinning effects, depending on timing and dosage, Naphthalene Acetic Acid can also promote fruit thinning by altering auxin balance in developing fruitlets.
This dual behavior makes application timing extremely important.
Naphthalene Acetic Acid improves application precision.
In species-dependent response, different crops (apple, pear, citrus, ornamental plants) respond differently to NAA concentrations.
Small changes in dose can shift effects from beneficial to phytotoxic.
Naphthalene Acetic Acid improves crop-specific management.
Naphthalene Acetic Acid can be degraded by microbial activity in soil, but persistence varies depending on temperature, moisture, and microbial community.
It is more stable than natural auxins but not permanently persistent.
Naphthalene Acetic Acid improves environmental fate understanding.
Naphthalene Acetic Acid is often compared with IAA (natural auxin) and IBA (rooting auxin) to study how stability and transport affect plant responses.
Each auxin has distinct physiological behavior.
Naphthalene Acetic Acid improves plant physiology research.
Naphthalene Acetic Acid is often formulated as salts or emulsifiable concentrates to improve water solubility and field application efficiency.
This improves spray uniformity and absorption.
In residue management, regulatory limits exist in many countries to ensure that treated crops remain safe for consumption.
Proper pre-harvest intervals are required depending on crop type.
This improves food safety compliance.
Melting point: 129–131.5 °C (lit.)
alpha: D25 −36.5° (c = 1 in methanol)
Boiling point: 646.3 ± 55.0 °C (Predicted)
Density: 1.34 ± 0.1 g/cm3 (Predicted)
storage temp.: 2–8°C
solubility: DMSO: 5 mg/mL (11.64 mM)
form: crystalline
pka: pK1: 4.236 (25°C)
color: light yellow
Naphthalene Acetic Acid is a synthetic plant hormone in the auxin family and is an ingredient in many commercial horticultural products; it is a rooting agent and used for the vegetative propagation of plants from stem and leaf cuttings.
Naphthalene Acetic Acid is also used for plant tissue culture.
The hormone Naphthalene Acetic Acid does not occur naturally, and, like all auxins, is toxic to plants at high concentrations.
In the United States, under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), products containing NAA require registration with the Environmental Protection Agency (EPA) as pesticides.
A proline derivative that is 4-(phenylsulfanyl)-L-proline in which the amine proton is replaced by a (2S)-3-(benzoylsulfanyl)-2-methylpropanoyl group. A prodrug for zofenoprilat.
Naphthalene Acetic Acid is one of the most widely used synthetic auxins because it is more stable than natural plant hormones like indole-3-acetic acid (IAA).
This stability allows it to remain active longer in plant tissues.
Naphthalene Acetic Acid improves effectiveness in field applications.
In root induction, Naphthalene Acetic Acid stimulates the formation of adventitious roots by activating cell division in the cambium and parenchyma tissues near the cut site.
This makes it highly effective in plant propagation systems.
Naphthalene Acetic Acid improves cloning and nursery production efficiency.
In fruit thinning, Naphthalene Acetic Acid is applied to reduce excess fruit load in crops such as apples and pears.
This improves fruit size, uniformity, and overall quality.
Naphthalene Acetic Acid improves market value of crops.
In anti-fruit drop applications, it helps prevent premature fruit abscission caused by environmental stress or hormonal imbalance.
Naphthalene Acetic Acid improves harvest yield and reduces losses.
In tissue culture systems, Naphthalene Acetic Acid is used in combination with cytokinins to control organ formation (roots vs shoots).
The balance of hormones determines plant development pathways.
Naphthalene Acetic Acid improves plant biotechnology control.
In ornamental horticulture, it is used to regulate plant shape, rooting, and growth behavior.
Naphthalene Acetic Acid improves aesthetic plant quality and production control.
In herbicide-related research, high concentrations of synthetic auxins like NAA can disrupt normal plant growth and cause abnormal cell expansion.
This is the basis for some auxin-type herbicide mechanisms.
Naphthalene Acetic Acid improves understanding of plant growth disruption.
In formulation science, Naphthalene Acetic Acid is often converted into soluble salts to improve water-based spray applications.
This improves practical usability in agriculture.
Naphthalene acetic acid is especially important in plant science because it acts as a highly persistent auxin signal that can strongly modify natural hormone gradients in plant tissues.
This ability to “override” local auxin balance is why it is so effective in controlled agriculture.
This improves intentional regulation of plant development.
At the physiological transport level, Naphthalene Acetic Acid is only partially polar in transport compared to natural auxin (IAA).
This means it does not move through plants in exactly the same regulated directional pathways, leading to stronger localized effects where it is applied.
Naphthalene Acetic Acid improves targeted application control.
In abscission zone regulation, Naphthalene Acetic Acid influences the enzymatic activity in cell separation layers between fruit and stem.
It can suppress or delay the activation of enzymes that break down cell walls, preventing fruit drop.
Naphthalene Acetic Acid improves harvest stability.
In dose-response behavior, Naphthalene Acetic Acid exhibits a classic hormone effect curve where very low doses stimulate growth regulation, while higher doses may inhibit growth or cause abnormal tissue responses.
This makes precise concentration control essential in agriculture.
Naphthalene Acetic Acid improves application safety and precision.
In plant stress interaction, Naphthalene Acetic Acid can interact with stress hormones like abscisic acid (ABA), sometimes altering drought or environmental stress responses indirectly through hormonal imbalance.
Naphthalene Acetic Acid improves understanding of plant stress physiology.
In tissue differentiation, Naphthalene Acetic Acid plays a key role in determining whether plant cells develop into roots, undifferentiated callus, or remain in a vegetative state when used with other hormones.
This depends strongly on auxin-to-cytokinin ratios.
This improves plant biotechnology control.
In comparative auxin stability, Naphthalene Acetic Acid is significantly more resistant to enzymatic degradation and light breakdown than IAA.
This makes it more predictable in field conditions but also increases the importance of correct dosage management.
Naphthalene Acetic Acid improves field reliability.
In crop-specific application sensitivity, apples, pears, citrus, and ornamentals all respond differently to NAA depending on developmental stage and environmental conditions.
This variability is why application protocols are highly standardized in commercial agriculture.
Naphthalene Acetic Acid improves precision agriculture practices.
In soil and environmental behavior, Naphthalene Acetic Acid can be broken down by microbial metabolism, but persistence depends on soil composition, temperature, and moisture levels.
It does not accumulate indefinitely but can remain active long enough to influence plant development if misused.
Naphthalene Acetic Acid improves environmental risk assessment.
In formulation science, Naphthalene Acetic Acid is often combined with surfactants and buffers to improve leaf absorption and stability in spray solutions.
Naphthalene Acetic Acid improves field efficiency and uptake consistency.
Uses Of Naphthalene Acetic Acid:
Naphthalene Acetic Acid is intended for use as an internal standard for the quantification of Zofenopril by GC- or LC-mass spectrometry.
Naphthalene Acetic Acid is widely used in agriculture for various purposes.
It is considered to be only slightly toxic but when at higher concentrations it can be toxic to animals.
Naphthalene Acetic Acid was shown when tested on rats via oral ingestion at 1000–5900 mg/kg.
Naphthalene Acetic Acid has been shown to greatly increase cellulose fiber formation in plants when paired with another phytohormone called gibberellic acid.
Because it is in the auxin family it has also been understood to prevent premature dropping and thinning of fruits from stems.
Naphthalene Acetic Acid is applied after blossom fertilization.
Increased amounts can actually have negative effects however, and cause growth inhibition to the development of plant crops.
Naphthalene Acetic Acid has been used on many different crops including apples, olives, oranges, potatoes, and various other hanging fruits.
In order for it to obtain its desired effects it must be applied in concentrations ranging from 20–100 μg/mL.
Naphthalene Acetic Acid present in the environment undergoes oxidation reactions with hydroxyl radicals and sulfate radicals.
Radical reactions of Naphthalene Acetic Acid were studied using pulse radiolysis technique.
Hydroxyl adduct radical was formed as the intermediate during the reaction of hydroxyl radical with Naphthalene Acetic Acid.
The intermediate naphthyl methyl radical was formed during the reaction of sulfate radical anion with Naphthalene Acetic Acid.
Naphthalene acetic acid is mainly used as a plant growth regulator, auxin analogue, rooting stimulant, fruit development regulator, and horticultural control agent because it directly influences plant hormone signaling pathways.
In rooting powders and gels, it is used to stimulate adventitious root formation in cuttings.
Naphthalene Acetic Acid improves propagation success and plant establishment.
In fruit thinning programs, it is used to reduce excessive fruit numbers in orchards.
Naphthalene Acetic Acid improves fruit size, quality, and uniformity.
In anti-fruit drop sprays, it is used to prevent premature fruit shedding before harvest.
This improves yield retention and harvesting efficiency.
In orchard management, it is used to balance vegetative growth and fruit production.
Naphthalene Acetic Acid improves crop consistency and productivity.
In tissue culture systems, it is used to induce root formation and control organ differentiation.
Naphthalene Acetic Acid improves plant regeneration efficiency.
In ornamental plant production, it is used to improve rooting and shape control.
Naphthalene Acetic Acid improves aesthetic and commercial value.
Naphthalene Acetic Acid is used in low concentrations for precise growth regulation.
This improves yield management and crop quality.
Naphthalene Acetic Acid is mainly used as a plant growth regulator, synthetic auxin, rooting stimulant, fruit development controller, and abscission regulator because it strongly influences plant hormonal signaling.
In rooting hormone products, it is used to stimulate adventitious root formation in cuttings.
Naphthalene Acetic Acid improves propagation success and plant establishment.
In fruit thinning applications, it is used to reduce excessive fruit load in orchards such as apples and pears.
Naphthalene Acetic Acid improves fruit size and uniformity.
In anti-fruit drop treatments, it is used to prevent premature fruit shedding before harvest.
This improves yield retention and harvest efficiency.
In orchard crop management, it is used to regulate growth balance between vegetative and reproductive structures.
Naphthalene Acetic Acid improves productivity and crop quality.
In tissue culture systems, it is used to control root formation and organ differentiation in combination with cytokinins.
Naphthalene Acetic Acid improves plant regeneration control.
In ornamental horticulture, it is used to improve rooting, growth form, and plant shaping.
Naphthalene Acetic Acid improves aesthetic and commercial value.
In commercial agriculture, it is applied in low concentrations for precise hormonal regulation of crops.
This improves yield control and farming efficiency.
Naphthalene acetic acid (NAA) is mainly used as a plant growth regulator, synthetic auxin, rooting stimulant, fruit development regulator, and abscission control agent because it directly affects plant hormone signaling pathways.
In rooting hormone treatments, it is used to stimulate adventitious root formation in plant cuttings.
Naphthalene Acetic Acid improves propagation success and plant establishment.
In fruit thinning programs, it is used to reduce excessive fruit numbers in crops such as apples and pears.
Naphthalene Acetic Acid improves fruit size, quality, and uniformity.
In anti-fruit drop sprays, it is used to prevent premature fruit abscission before harvest.
Naphthalene Acetic Acid improves yield retention and harvesting efficiency.
In orchard management systems, it is used to regulate balance between vegetative growth and fruit production.
Naphthalene Acetic Acid improves crop productivity and consistency.
In tissue culture applications, it is used to control root formation and organ differentiation in combination with cytokinins.
Naphthalene Acetic Acid improves plant regeneration efficiency.
In ornamental plant production, it is used to improve rooting success and plant shape control.
Naphthalene Acetic Acid improves aesthetic and commercial value.
In commercial agriculture, it is used at very low concentrations for precise regulation of plant development.
Naphthalene Acetic Acid improves yield management and crop quality.
Safety Profile Of Naphthalene Acetic Acid:
Naphthalene Acetic Acid is considered a moderately hazardous plant growth regulator, mainly due to its biological activity and irritation potential rather than extreme toxicity.
It may cause eye and skin irritation, especially in concentrated powder or solution form.
This improves safe handling awareness.
Inhalation of dust may cause respiratory irritation, coughing, or throat discomfort.
Naphthalene Acetic Acid improves occupational exposure control.
Ingestion may lead to gastrointestinal effects such as nausea, vomiting, and abdominal pain, depending on dose.
Naphthalene Acetic Acid improves ingestion safety awareness.
At high exposure levels, synthetic auxins like NAA can disrupt normal cellular regulation due to their strong hormonal activity in plants.
This is the basis of both its agricultural usefulness and toxicity potential.
Naphthalene Acetic Acid improves biological risk understanding.
It is considered toxic to aquatic organisms, so environmental release should be controlled.
This improves environmental protection awareness.
The compound is generally chemically stable under normal storage conditions, but should be kept away from strong oxidizers and excessive heat.
This improves storage safety.
Naphthalene Acetic Acid is a bioactive synthetic auxin with moderate hazard potential requiring standard chemical handling precautions to avoid irritation and environmental impact, especially in agricultural applications.
