NAA Solution (1mg/mL) - BioReagent, 1 mg/mL in water , CAS No.86-87-3

CAS: 86-87-3 Cat. No.: N1528791 Formula: C₁₂H₁₀O₂ Molecular Weight: 186.21 Beilstein Registry Number: 1308415 EC Number: 201-705-8

GRADE & PURITY BioReagent, 1 mg/mL in water

Storage

Room temperature

Shipped In

Normal

Application

1050

Overview

Pure 1-Naphthaleneacetic acid (NAA) is colorless acicular crystals, while the industrial grade is yellowish-brown acicular crystals. It is soluble in hot water, ethanol, acetic acid, acetone and benzene, and serves as a broad-spectrum plant growth regulator. It can be applied to wheat and rice to increase effective tillers, raise the spike rate, promote grain plumpness and achieve significant yield increase. It also boosts yields of sweet potato and cotton. For solanaceous and melon crops, it prevents flower and fruit drop, induces seedless fruit formation, and enhances plant tolerance to drought, waterlogging, salinity, alkalinity and lodging.

Operating Procedures (For Reference Only):

1. For wheat: Soak seeds in 20 mg/L solution for 10–12 h, air-dry before sowing. Spray once at 25 mg/kg before jointing stage. After anthesis, spray flag leaves and panicles with 30 mg/kg solution to prevent lodging and improve seed setting rate.

2. For rice: Soak rice seedlings in 10 mg/L solution for 6 h. Transplanted seedlings recover rapidly and develop robust stems.

3. For cotton: Spray plants with 10–20 mg/L solution 2–3 times during full blooming stage at an interval of 10 days to prevent boll abscission.

4. For sweet potato: Soak the lower part (3 cm) of sweet potato seedlings in 10 mg/L solution for 6 h before transplanting to improve survival rate and yield.

5. For tomato and melons: Spray flowers with 10–30 mg/L solution to prevent flower drop and promote fruit setting.

6. For fruit trees: Spray the whole plant with 5–20 mg/L solution 5–21 days before harvest to avoid pre-harvest fruit drop.

7. For cuttings of tea, mulberry, oriental arborvitae, oak, metasequoia, etc.: Immerse the base (3–5 cm) of cuttings in 25–500 mg/L solution for 24 h to promote rooting and raise survival rate.

Precautions:

1. If the consumption per use is small, the product may be properly aliquoted before use.

2. Wear laboratory coat and disposable gloves during operation for your safety and health.

3. This product is for research use only. Any other application is prohibited.

Specifications

Specifications & Purity

BioReagent, 1 mg/mL in water

Stability And Storage

Store at room temperature long term (12 months)

Storage

Room temperature

Shipped In

Normal

Grade

BioReagent

Product Line

Biological Products

Names and Identifiers

Isomeric SMILES

C1=CC=C2C(=C1)C=CC=C2CC(=O)O

WGK Germany

3

RTECS

QJ0875000

Alternate CAS

86-87-3

Molecular Weight

186.21

Beilstein

1308415

Reaxy-Rn

1308415

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1308415&ln=

Chemical and Physical Properties

• Melt Point(°C): 132°C

Application Protocols

Item-specific validated protocols: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for using a 1 mg/mL NAA stock (literature; example calculations)

• Stock concentration: 1 mg/mL corresponds to ~5.37 mM if the active is 1‑naphthaleneacetic acid (MW ~186.21 g/mol; literature). Adjust if your lot specifies a different MW or salt form.
• Working solutions:
  • 1 µM working: Add 1 µL of stock per 5.37 mL of medium (approximate). For 100 mL, add ~18.6 µL.
  • 10 µM working: Add 10 µL of stock per 5.37 mL of medium. For 100 mL, add ~186 µL.
  • 100 µM working: Add 100 µL of stock per 5.37 mL of medium. For 100 mL, add ~1.86 mL.
• Procedure tips:
  • Mix thoroughly and add stock last to avoid local supersaturation. If precipitation is observed, pre-dilute the stock 1:10 in the destination medium before adding the remainder.
  • Keep final carrier concentration low (commonly ≤0.1–0.5% v/v). Include a vehicle control at the same carrier level.
  • Protect from light during preparation and incubation.

Documentation

• Confirm the solvent system, exact concentration, and any preservatives for your lot on the CoA before applying these calculations.

Biological Roles

Literature overview for NAA (1‑naphthaleneacetic acid)

• Mode of action: Synthetic auxin that mimics indole-3-acetic acid (IAA). Binds to TIR1/AFB F-box proteins in the SCF ubiquitin ligase complex, promoting interaction with Aux/IAA transcriptional repressors and their subsequent ubiquitination and proteasomal degradation.
• Downstream effects: Rapid transcriptional activation of auxin-responsive genes (AuxRE-containing promoters), alteration of cell elongation, division, and differentiation programs.
• Phenotypic outcomes (context-dependent): Root initiation and lateral root formation, callus induction, inhibition of axillary bud outgrowth, and tropic responses in seedlings.
• Transport: Unlike IAA, NAA is less susceptible to enzymatic degradation and has altered transport characteristics (reduced conjugation/metabolism in many species), making it useful for sustained auxin responses in experiments.
• Concentration dependence: Biphasic responses are common; low doses stimulate root primordia, whereas high doses can be inhibitory or induce callus (literature observations). Always determine dose–response for each species/tissue.

Item-specific note

• This product provides a ready-to-use 1 mg/mL solution to streamline preparation of working concentrations for plant biology assays. Exact solvent and any stabilizers are Not specified for this item; refer to CoA/Spec Sheet.

Buffer Applications

Not a primary buffering agent

• NAA is a weak aromatic carboxylic acid used as a bioactive modulator rather than as a buffer component.

Literature notes

• Acid–base properties: pKa ~4.2–4.3. While this places its maximum buffering capacity near pH ~4.2, the solubility of the free acid is limited at low ionic strength and neutral pH. The sodium salt is more water-soluble but still not commonly used as a laboratory buffer.
• Practical implication: Inclusion of NAA at bioactive concentrations (nM–100 µM) will not appreciably contribute to buffer capacity in most media. Adjust pH with standard buffers (e.g., MES pH 5–6, phosphate pH 6–7.5) and add NAA separately as a supplement.

Item-specific

• Because the carrier solvent and pH are Not specified for this item, verify that adding aliquots of the 1 mg/mL solution does not perturb the receiving buffer’s pH or cause precipitation. Conduct small-scale compatibility tests if working at very low ionic strength or low temperature.

Green Alternatives

Context

• The environmental footprint of this product is dominated by the choice of carrier solvent and disposal practices rather than NAA itself. The solvent system is Not specified for this item; refer to CoA/Spec Sheet.

Greener handling options (literature guidance)

• Prefer ethanol or water-based alkaline solutions (sodium NAA) over high-boiling, persistent solvents when compatible with the assay.
• Use minimal organic cosolvent in final media (≤0.1% v/v when feasible) to reduce VOC emissions and cytotoxicity to plant tissues.
• Prepare concentrated stocks to reduce packaging and transport mass, then dilute at point-of-use.

Comparison (literature, illustrative)

• Carrier: Ethanol — Renewable feedstock, readily biodegradable; flammable; low toxicity at trace levels.
• Carrier: DMSO — Excellent solvency; higher boiling point complicates waste handling; may affect membrane permeability in bioassays.
• Carrier: Aqueous Na-salt — Lowest VOC; requires pH control; potential ionic strength effects.

Waste and EHS

• Collect unused auxin solutions as halogen-free organic waste or aqueous-organic waste per institutional policy. Avoid release to soil/water to prevent unintended plant growth effects.

Pharmaceutical Uses

Scope

• This product is designated For research use only and BioReagent grade. It is not intended for human or veterinary use, clinical diagnostics, or as an active pharmaceutical ingredient.

Context (literature)

• NAA (1‑naphthaleneacetic acid) is a plant growth regulator used in agricultural and plant research settings. It does not have a recognized role as a pharmaceutical excipient. Accordingly, pharmacopeial monographs and GMP manufacturing considerations are generally not applicable.

Laboratory/formulation relevance

• In research formulations (e.g., plant tissue culture media), NAA is added as a bioactive supplement rather than a functional excipient. Ensure that any carrier solvent introduced by the 1 mg/mL stock remains within tolerated limits for the biological system under study.

Item-specific statement

• No pharmacopeial grade or clinical-use claims are made for this item. All uses must be confined to laboratory research in appropriately equipped facilities.

Physical Properties

Item-specific (as supplied)

• Concentration: 1 mg/mL (specified for this item)
• Appearance, solvent, pH, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

Literature values for neat NAA (for context; not item specifications)

• Physical state: Crystalline solid
• Melting point: ~135–137 °C (literature)
• Boiling point: Decomposes before boiling (literature)
• pKa (carboxyl): ~4.2–4.3 at 25 °C (literature)
• LogP (octanol/water): ~2.7 (literature)
• Aqueous solubility: Low at neutral pH; increased solubility in basic aqueous media (e.g., NaOH) and in polar organics (ethanol, DMSO) (literature)

Implications for use

• Because the product is a ready solution, physical behavior will be governed by the solvent system, which is not specified here. Verify solvent compatibility with your assay matrices (plant tissue culture media, hydroponic solutions, or biochemical buffers) and plastics/metals in your workflow.
• If working near neutral pH, note that free-acid NAA is sparingly water-soluble; many protocols employ ethanol or DMSO carrier or convert to its sodium salt to improve aqueous handling (literature guidance).

Quality & Grades

Item-specific

• Grade/Purity: BioReagent (specified for this item)
• Concentration: 1 mg/mL ready-to-use solution

What BioReagent grade generally implies

• Intended for life-science and biochemical workflows where consistent composition and low bioburden/trace impurities are important. While not equivalent to clinical/pharmaceutical grade, BioReagent materials are typically qualified for research assays, tissue culture workflows (when specified), and analytical studies.

Considerations for this item

• UV background and excipient profile: Not specified for this item; refer to CoA/Spec Sheet for details such as solvent identity, UV transparency, and any stabilizers or preservatives.
• Endotoxin/bioburden: Not specified for this item; consult CoA if sterility or endotoxin limits are critical for your application.
• Suitability: The ready-to-use 1 mg/mL format reduces weighing variability and improves dose reproducibility for routine auxin-response studies, plant tissue culture supplementation, or bioassays, provided the solvent system is compatible with the matrix.

Documentation

• For assay-critical parameters (e.g., solvent identity, pH, residual metals, UV cutoff), use the Certificate of Analysis/Specification Sheet that accompanies your lot.

Reaction & Applications

Applicability

• As a prepared 1 mg/mL NAA solution intended for life-science use, this product is not typically employed as a solvent or general-purpose organic reagent in synthesis.

Biological/assay applications (literature)

• Plant biology: Widely used as a synthetic auxin to probe auxin-responsive gene expression, root initiation, callus induction, and organogenesis in plant tissue culture and seedling assays.
• Chemical biology: Employed to modulate TIR1/AFB auxin receptor complexes to trigger Aux/IAA protein degradation in auxin-signaling studies.

Practical tips

• Prepare serial dilutions into assay medium to reach target concentrations (often nM to low-100 µM, literature). Mix thoroughly to avoid localized precipitation, especially if the carrier is DMSO or ethanol.
• Light sensitivity: Auxins and related aromatics can show light-induced degradation; minimize light exposure during handling and incubation (cover flasks/plates with foil when feasible).
• Adsorption: Hydrophobic acids can adsorb to plastics at low nM–µM levels. Pre-rinse plastics with dilute working solution or use low-bind labware to improve dose accuracy.

If using in chemical synthesis (less common)

• The carboxylic acid can be converted to esters or amides (e.g., probe conjugates) via standard coupling methods (DCC/EDC/HATU) under mild conditions.

Reaction Conditions

Applicability

• For this BioReagent 1 mg/mL solution, “reaction conditions” are best interpreted as biological assay conditions rather than organic reaction parameters.

Literature guidance for biological use

• Working ranges: Auxin responses are commonly evaluated from low nanomolar to ~100 µM, depending on plant species, tissue type, and endpoint (gene expression, root initiation, callus induction).
• Media compatibility: Effective in standard plant tissue culture media (e.g., MS or ½ MS) and hydroponic solutions. Organic carrier (ethanol or DMSO) should typically remain ≤0.1–0.5% v/v final to minimize solvent effects.
• Incubation: Light-sensitive; protect stock and treated samples from strong light. Temperature consistent with growth conditions (often 20–25 °C for Arabidopsis; species-dependent).
• Controls: Include vehicle-only controls at matching carrier concentration and pH-matched blanks if sodium salt stocks are used.

Chemical transformation conditions (if derivatizing; literature)

• Esterification: Alcohol, catalytic acid, reflux or Steglich conditions at 0–25 °C.
• Amide coupling: EDC/HOBt or HATU in DMF/DCM, base (DIPEA), 0–25 °C, 1–12 h.

Item-specific note

• Solvent, pH, and stabilizers for this stock are Not specified for this item; verify compatibility empirically.

Safety & Handling

Item-specific hazard data

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS and CoA/Spec Sheet for authoritative information.

General safety guidance (literature/context)

• NAA (1‑naphthaleneacetic acid) is an organic acid/plant growth regulator. Avoid inhalation of mists/aerosols and contact with skin/eyes. Handle solutions in a chemical fume hood when aerosolization or heating is possible.
• Personal protective equipment: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use splash protection for bulk handling.
• Storage incompatibilities: Avoid strong oxidizers and strong bases/acids unless neutralization is intended. Do not mix with strong reducing agents or reactive acylation agents without controls.
• Spill/cleanup: Absorb small spills with inert material (vermiculite), collect for disposal. Rinse residues with appropriate solvent while preventing environmental release.
• First-aid overview: If on skin/eyes, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always follow institutional SOPs and consult the SDS for this specific item.
• Environmental note: Auxin analogs can affect plant growth; prevent uncontrolled discharge to the environment.

Solvent Selection

Applicability to this item

• The product is already supplied as a 1 mg/mL solution; the primary solvent and any cosolvents are Not specified for this item; refer to CoA/Spec Sheet.

General guidance (literature) for NAA handling when preparing additional dilutions

• Polarity/solubility: NAA is a weak aromatic carboxylic acid with low water solubility at neutral pH but dissolves readily in ethanol, methanol, acetone, and DMSO; aqueous solubility increases upon deprotonation (e.g., NaOH to form sodium NAA).
• Typical carriers for biological assays: Ethanol (≤0.1–1% v/v final), DMSO (≤0.1–0.5% v/v final), or pre-neutralized aqueous stock (sodium salt) to maintain media compatibility.
• Dielectric considerations: Moving from DMSO (ε ~47) to ethanol (ε ~25) may affect miscibility and precipitation upon dilution into high-ionic-strength media. Pre-dilute into a small volume of target matrix to minimize local supersaturation.

When to choose alternatives

• For strictly aqueous systems sensitive to organic cosolvent, prepare NAA as the sodium salt or adjust pH slightly basic to ensure solubility (verify biological tolerance).
• For optical assays near 260–300 nm, ethanol carriers may provide lower background than DMSO; confirm by blank scans with your instrument setup.

Storage & Reconstitution

Item-specific

• Storage conditions: Room temperature (as provided in Product Data)
• Shipped: Normal (ambient) conditions
• Format: Ready-to-use solution at 1 mg/mL; no reconstitution required

Best practices (literature/general guidance for auxin solutions)

• Protect from light: Store in amber vials or wrap containers in foil to minimize photodegradation.
• Container: Use tightly sealed, chemically compatible containers; minimize headspace if extended storage is anticipated.
• Freeze–thaw: Not applicable to dry material; for solutions, avoid repeated freeze–thaw cycling. If cold storage is later chosen, aliquot to single-use portions.
• Stability: Specific shelf-life, pH, and solvent identity are Not specified for this item; refer to CoA/Spec Sheet. Periodically inspect for precipitate, discoloration, or unexpected odor; discard if changes occur.
• Handling: Bring to working temperature before opening to prevent condensation. Use sterile technique if adding to sterile media and sterility is required by your application.

Disposal

• Dispose of unused solution and contaminated materials according to institutional chemical waste procedures; avoid environmental release due to plant bioactivity.

Structure & Identity

Item-specific (from Product Data)

• Product: NAA Solution (1 mg/mL)
• Grade: BioReagent
• Format: Ready-to-use solution at 1 mg/mL
• CAS, InChIKey, SMILES, Molecular formula, Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Common identity in literature (for NAA = 1‑naphthaleneacetic acid; informational)

• Synonyms: 1-Naphthylacetic acid; α-naphthaleneacetic acid (auxin analog)
• Molecular formula (literature): C12H10O2
• Molecular weight (literature): ~186.21 g/mol
• SMILES (literature): OC(=O)CH2c1cccc2ccccc12
• InChIKey (literature): BHMQWCSIRUMIHO-UHFFFAOYSA-N

Structural features (literature)

• Core: Naphthalene bicyclic aromatic ring system fused from two benzene rings.
• Functional group: Benzylic acetic acid side chain (–CH2–CO2H) at the 1-position; weak aromatic carboxylic acid.
• 2D description: A carboxymethyl substituent attached to the α-position of naphthalene; no stereocenters; fully aromatic ring system with conjugation across both rings.

Notes

• The above identifiers and features describe neat 1‑naphthaleneacetic acid commonly abbreviated NAA in plant biology. The supplied item is a 1 mg/mL solution; exact solvent and any additives are not specified in the Product Data.

Synthetic Utility

While this product is primarily intended for biological assays, the NAA scaffold (literature perspective) offers useful synthetic handles:

• Functional group: Benzylic acetic acid (–CH2–CO2H) enables standard carboxylic acid transformations: esterification (Fischer or Steglich), amide coupling (EDC/HOBt, HATU), and conversion to acid chlorides (SOCl2, oxalyl chloride) for further derivatization.
• Probe derivatization: Formation of fluorescent or affinity tags via amide/ester linkages to explore auxin transport, receptor binding, or to immobilize NAA on solid supports.
• Cross-coupling strategies: The naphthalene core can be functionalized (prior to acetic acid installation) using electrophilic substitution or directed ortho-lithiation, enabling synthesis of substituted NAA analogs with tuned potency/transport.
• Salt formation: Sodium or potassium salts enhance aqueous solubility for biochemical assays without modifying the aromatic core; reversible upon pH adjustment.

Item-specific considerations

• Because this item is a 1 mg/mL solution with unspecified solvent system, it is not optimized as a starting material for multi-step organic synthesis. For synthetic campaigns, procure neat NAA or define the solvent composition before use.

Target Specificity

Item-specific validated targets/applications: Not specified for this item; refer to CoA/Spec Sheet.

Literature context for NAA (biological target)

• Primary target pathway: Auxin perception via TIR1/AFB F-box proteins in the SCF E3 ubiquitin ligase complex.
• Mechanism: NAA promotes co-receptor complex formation between TIR1/AFB and Aux/IAA repressors, facilitating ubiquitination and proteasomal degradation of Aux/IAAs. This derepresses ARF transcription factors, altering expression of auxin-responsive genes.
• Selectivity considerations: Relative to natural IAA, NAA often exhibits increased metabolic stability and sustained signaling, but potency and transport can vary by tissue and species. Off-target effects may arise at supra-physiological concentrations; establish dose–response curves and include vehicle controls.