1,4-Dihydroxy-2-naphthoic acid

Cat. No.: HY-W014701 Purity: 99.60%: Data Sheet
COA

SDS
Handling Instructions
FAQs
Technical Support

1,4-Dihydroxy-2-naphthoic acid is an aryl hydrocarbon receptor (AhR) agonist. 1,4-Dihydroxy-2-naphthoic acid is also a bacterially derived metabolite and has anti-inflammatory activity.

For research use only. We do not sell to patients.

1,4-Dihydroxy-2-naphthoic acid Chemical Structure

CAS No. : 31519-22-9

Size	Stock	Quantity

Free Sample (0.1 - 0.2 mg)	Apply Now
Solid + Solvent (Highly Recommended)
10 mM * 1 mL in DMSO ready for reconstitution	In-stock	Estimated Time of Arrival: December 31
Solution
10 mM * 1 mL in DMSO	In-stock	Estimated Time of Arrival: December 31
Solid
1 g	In-stock	Estimated Time of Arrival: December 31
5 g	Get quote
10 g	Get quote

or Bulk Inquiry

* Please select Quantity before adding items.

This product is a controlled substance and not for sale in your territory.

Other Forms of 1,4-Dihydroxy-2-naphthoic acid:

1,4-Dihydroxy-2-naphthoic acid (Standard) Get quote

Featured Recommendations

•Related Screening Libraries:

•Related Small Molecules:

•Related Proteins:

View All Cytochrome P450 Isoform Specific Products:

View All Isoforms

CYP1 CYP2 CYP3 CYP4 CYP11 CYP17 Aromatase/CYP19A1 CYP26 CYP51 CYP1A2 CYP2D6 CYP2C9 CYP2C19 CYP3A4 CYP17A1

View All Interleukin Related Isoform Specific Products:

View All Isoforms

IL-1 IL-2 IL-3 IL-4 IL-5 IL-6 IL-8 IL-10 IL-12 IL-13 IL-15 IL-17 IL-23 IL-7 IL-33 IL-22

Biological Activity
Purity & Documentation
References
Customer Review

Description

1,4-Dihydroxy-2-naphthoic acid is an aryl hydrocarbon receptor (AhR) agonist. 1,4-Dihydroxy-2-naphthoic acid is also a bacterially derived metabolite and has anti-inflammatory activity^[1].

In Vitro

1,4-Dihydroxy-2-naphthoic acid (25-1000 μM, 18-24 h) induces > 70% of the response for CYP1A1 and CYP1B1 in both YAMC and Caco2 cells^[2].
1,4-Dihydroxy-2-naphthoic acid (100 μM, 24 h) inhibits IL-1β, IL-6, IL-23, p19 and IL-17A mRNA levels in LPS (HY-D1056)-stimulated RAW264.7 cells^[4].
1,4-Dihydroxy-2-naphthoic acid (48-72 h) inhibits proliferation against HaCaT, NCTC 2544, Hs-69 and PIG1 cells with IC₅₀s of 38.94, 46,80, 226.3 and 23.98 μM at 72 h^[5].
1,4-Dihydroxy-2-naphthoic acid (15-120 μM, 9-72 h) induces apoptosis and causes G0/G1 Cell cycle arrest in HaCaT cells in time and dose dependent manners^[5].
1,4-Dihydroxy-2-naphthoic acid (30-240 μM, 24-48 h) decreases MMP, increases DNA fragmentation and causes nuclear translocation of AIF and endoG in HaCaT cells^[5].
1,4-Dihydroxy-2-naphthoic acid (20-100 μM, 72 h) exhibits relatively low skin irritation, that significantly induces the release of IL-1α only at a concentration of 60 μM in NCTC2544cells^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

RT-PCR^[2]

Cell Line:	YAMC and Caco2 cells
Concentration:	25, 50, 100, 250, 500, 1000 μM
Incubation Time:	18 h
Result:	Induced Cyp1a1 and Cyp1b1 in both cells. Completely eliminated the induction effects on Cyp1a1 and Cyp1b1 when the AhR was knocked out.

Western Blot Analysis^[2]

Cell Line:	YAMC and Caco2 cells
Concentration:	500 μM
Incubation Time:	24 h
Result:	Induced Cyp1a1 and Cyp1b1 expression in both cells.

RT-PCR^[4]

Cell Line:	LPS-stimulated RAW264.7 cells
Concentration:	100 μM
Incubation Time:	24 h
Result:	Inhibited IL-1β, IL-6, IL-23p19 and IL-17A mRNA levels in RAW264.7 cells.

Apoptosis Analysis^[5]

Cell Line:	HaCaT cells
Concentration:	30, 60 and 120 μM
Incubation Time:	9, 24 and 72 h
Result:	Increased in nuclear fluorescence from dark blue to light blue/white (chromatin condensation) at 30 and 60 μM. Formed apoptotic bodies at 120 μM. Increased apoptosis ratio time dependently. Activated Caspase-8 and Caspase-9 and cleavage PARP and Bid.

Apoptosis Analysis^[5]

Cell Line:	HaCaT cells
Concentration:	15, 30, 60 and 120 μM
Incubation Time:	24 h
Result:	Dose-dependently induced G0/G1 cell cycle arrest. Upregulated p21, while downregulated Cyclin D1/D3 and Cdk4.

In Vivo

1,4-Dihydroxy-2-naphthoic acid (20 mg/kg, p.o., for 5-10 weeks) successfully prevents and reverses unpredictable chronic mild stress (UCMS)-induced anhedonia-like behavior in mice^[1].
1,4-Dihydroxy-2-naphthoic acid (2 mg/kg, p.o., for 14 days) reduces inflammation in mice with colitis by suppressing macrophage-derived proinflammatory cytokines^[4].
1,4-Dihydroxy-2-naphthoic acid (20 mg/kg, p.o., for 3 weeks) prevents mice motor dysfunction induced by MPTP (HY-W114750)^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	UCMS model established in female C57BL/6 mice (6-7 weeks)^[1]
Dosage:	20 mg/kg
Administration:	Oral administration (p.o.), once daily, 3 weeks prior to UCMS or 2 weeks after UCMS, for 5-10 weeks
Result:	Did not exhibit a reduction in sucrose preference. Restored the activity of Ca-ATPase and glycogen levels, and reduced phospholipase and lipid peroxides. Did not significantly affect open field test (OFT), marble bury (MB) and novelty-induced hypophagia (NIH) behaviors. Had no significant effect on the light/dark (L/D) test or on anxiety behaviors in the elevated plus maze (EPM). Had a significant effect on spatial learning in unstressed animals.

Animal Model:	Colitis model established in 8-week male interleukin-10-deficient mice^[4]
Dosage:	2 mg/kg
Administration:	Oral administration (p.o.) with water freely available, for 14 days
Result:	Significantly reduced the inflammation score. Significantly reduced F4/80^⁺ cells and VCAM-1 expression. Significantly inhibited IL-1β, IL-6, TNF-α, IL-23p19 and IL-17A mRNA levels.

Animal Model:	Parkinson's disease (PD) model established in male C57BL/6 mice^[6]
Dosage:	20 mg/kg
Administration:	Oral administration (p.o.), for 3 weeks
Result:	Prevented MPTP-induced deficits in the motor pole test and in the adhesive strip removal test. Improved balance beam performance and completely prevented MPTP-induced reduction in stride length.

Molecular Weight

204.18

Formula

C₁₁H₈O₄

CAS No.

31519-22-9

Appearance

Solid

Color

Gray to brown

SMILES

OC1=CC(C(O)=O)=C(O)C2=CC=CC=C21

Structure Classification

Ketones, Aldehydes, Acids

Initial Source

Propionibacterium freudenreichii

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, sealed storage, away from moisture

*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

Solvent & Solubility

In Vitro:

DMSO : 175 mg/mL (857.09 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	4.8976 mL	24.4882 mL	48.9764 mL
5 mM	0.9795 mL	4.8976 mL	9.7953 mL
10 mM	0.4898 mL	2.4488 mL	4.8976 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molarity Calculator
Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)

Volume _(start)

Concentration _(final)

Volume _(final)

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Calculation results:

Working solution concentration: mg/mL

Purity & Documentation

Purity: 99.60%

Select Batch:

Data Sheet (286 KB) SDS (393 KB)

COA (252 KB) HNMR (291 KB) LCMS (97 KB)

Handling Instructions (2659 KB)

References

[1]. Madison CA, et al. 3,3'-Diindolylmethane and 1,4-dihydroxy-2-naphthoic acid prevent chronic mild stress induced depressive-like behaviors in female mice. J Affect Disord. 2022 Jul 15;309:201-210. [Content Brief]

[2]. Cheng Y, et al. Editor's Highlight: Microbial-Derived 1,4-Dihydroxy-2-naphthoic Acid and Related Compounds as Aryl Hydrocarbon Receptor Agonists/Antagonists: Structure-Activity Relationships and Receptor Modeling. Toxicol Sci. 2017 Feb;155(2):458-473. [Content Brief]

[3]. Kang JE, et al. A Novel Lactobacillus casei LP1 Producing 1,4-Dihydroxy-2-Naphthoic Acid, a Bifidogenic Growth Stimulator. Prev Nutr Food Sci. 2015 Mar;20(1):78-81. [Content Brief]

[4]. Okada Y, et al. 1,4-Dihydroxy-2-naphthoic acid from Propionibacterium freudenreichii reduces inflammation in interleukin-10-deficient mice with colitis by suppressing macrophage-derived proinflammatory cytokines. J Leukoc Biol. 2013 Sep;94(3):473-80. [Content Brief]

[5]. Mok CF, et al. 1,4-dihydroxy-2-naphthoic Acid Induces Apoptosis in Human Keratinocyte: Potential Application for Psoriasis Treatment. Evid Based Complement Alternat Med. 2013;2013:792840. [Content Brief]

[6]. Madison CA, et al. 1,4-dihydroxy-2-naphthoic acid prevents 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced motor function deficits. Behav Pharmacol. 2025 Feb 1;36(1):40-46. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

DMSO	1 mM	4.8976 mL	24.4882 mL	48.9764 mL	122.4410 mL
	5 mM	0.9795 mL	4.8976 mL	9.7953 mL	24.4882 mL
	10 mM	0.4898 mL	2.4488 mL	4.8976 mL	12.2441 mL
	15 mM	0.3265 mL	1.6325 mL	3.2651 mL	8.1627 mL
	20 mM	0.2449 mL	1.2244 mL	2.4488 mL	6.1220 mL
	25 mM	0.1959 mL	0.9795 mL	1.9591 mL	4.8976 mL
	30 mM	0.1633 mL	0.8163 mL	1.6325 mL	4.0814 mL
	40 mM	0.1224 mL	0.6122 mL	1.2244 mL	3.0610 mL
	50 mM	0.0980 mL	0.4898 mL	0.9795 mL	2.4488 mL
	60 mM	0.0816 mL	0.4081 mL	0.8163 mL	2.0407 mL
	80 mM	0.0612 mL	0.3061 mL	0.6122 mL	1.5305 mL
	100 mM	0.0490 mL	0.2449 mL	0.4898 mL	1.2244 mL