Naphthalene
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MedKoo CAT#: 591613

CAS#: 91-20-3

Description: Naphthalene is an organic compound with formula C ₁₀H ₈. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass.

Chemical Structure

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Naphthalene
CAS# 91-20-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 591613
Name: Naphthalene
CAS#: 91-20-3
Chemical Formula: C10H8
Exact Mass: 128.06
Molecular Weight: 128.174
Elemental Analysis: C, 93.71; H, 6.29

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Synonym: Naphthalene; NSC 37565; NSC-37565; NSC37565

IUPAC/Chemical Name: Naphthalene

InChi Key: UFWIBTONFRDIAS-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H

SMILES Code: C12=CC=CC=C1C=CC=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Naphthalene is an organic compound with formula C ₁₀H ₈.
In vitro activity: For this purpose, in this study, a series of 10 new naphthalene-chalcone derivatives were synthesized and their anticancer-antibacterial-antifungal properties were investigated. Among the compounds, compound 2j showed activity against the A549 cell line with an IC50 = 7.835 ± 0.598 μM. This compound also has antibacterial and antifungal activity. Reference: ACS Omega. 2023 Feb 13;8(7):6669-6678. https://pubmed.ncbi.nlm.nih.gov/36844559/
In vivo activity: In individual lung regions, this study found metabolomic changes in microdissected mouse lung conducting airways and parenchyma obtained from animals sacrificed at 3 timepoints following naphthalene treatment. Importantly, temporal changes were found to be highly distinct for male and female mice with males exhibiting predominant treatment-specific changes only at 2 h postexposure. In females, metabolomic changes persisted until 6 h postnaphthalene treatment, which may explain the previously characterized higher susceptibility of female mice to naphthalene toxicity. In both males and females, treatment-specific changes corresponding to lung remodeling, oxidative stress response, and DNA damage were observed. Reference: Toxicol Sci. 2021 Nov 24;184(2):214-222. https://pubmed.ncbi.nlm.nih.gov/34498071/

Preparing Stock Solutions

The following data is based on the product molecular weight 128.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Osmaniye D, Sağlık BN, Khalilova N, Levent S, Bayazıt G, Gül ÜD, Özkay Y, Kaplancıklı ZA. Design, Synthesis, and Biological Evaluation Studies of Novel Naphthalene-Chalcone Hybrids As Antimicrobial, Anticandidal, Anticancer, and VEGFR-2 Inhibitors. ACS Omega. 2023 Feb 13;8(7):6669-6678. doi: 10.1021/acsomega.2c07256. PMID: 36844559; PMCID: PMC9947975. 2. El-Sheref EM, Ameen MA, El-Shaieb KM, Abdel-Latif FF, Abdel-Naser AI, Brown AB, Bräse S, Fathy HM, Ahmad I, Patel H, Gomaa HAM, Youssif BGM, Mohamed AH. Design, Synthesis and Biological Evaluation of Syn and Anti-like Double Warhead Quinolinones Bearing Dihydroxy Naphthalene Moiety as Epidermal Growth Factor Receptor Inhibitors with Potential Apoptotic Antiproliferative Action. Molecules. 2022 Dec 10;27(24):8765. doi: 10.3390/molecules27248765. PMID: 36557897; PMCID: PMC9788418. 3. Stevens NC, Edwards PC, Tran LM, Ding X, Van Winkle LS, Fiehn O. Metabolomics of Lung Microdissections Reveals Region- and Sex-Specific Metabolic Effects of Acute Naphthalene Exposure in Mice. Toxicol Sci. 2021 Nov 24;184(2):214-222. doi: 10.1093/toxsci/kfab110. PMID: 34498071; PMCID: PMC8633889. 4. Kovalchuk N, Zhang QY, Van Winkle L, Ding X. Contribution of Pulmonary CYP-mediated Bioactivation of Naphthalene to Airway Epithelial Injury in the Lung. Toxicol Sci. 2020 Oct 1;177(2):334-346. doi: 10.1093/toxsci/kfaa114. PMID: 32974682; PMCID: PMC7548286.
In vitro protocol: 1. Osmaniye D, Sağlık BN, Khalilova N, Levent S, Bayazıt G, Gül ÜD, Özkay Y, Kaplancıklı ZA. Design, Synthesis, and Biological Evaluation Studies of Novel Naphthalene-Chalcone Hybrids As Antimicrobial, Anticandidal, Anticancer, and VEGFR-2 Inhibitors. ACS Omega. 2023 Feb 13;8(7):6669-6678. doi: 10.1021/acsomega.2c07256. PMID: 36844559; PMCID: PMC9947975. 2. El-Sheref EM, Ameen MA, El-Shaieb KM, Abdel-Latif FF, Abdel-Naser AI, Brown AB, Bräse S, Fathy HM, Ahmad I, Patel H, Gomaa HAM, Youssif BGM, Mohamed AH. Design, Synthesis and Biological Evaluation of Syn and Anti-like Double Warhead Quinolinones Bearing Dihydroxy Naphthalene Moiety as Epidermal Growth Factor Receptor Inhibitors with Potential Apoptotic Antiproliferative Action. Molecules. 2022 Dec 10;27(24):8765. doi: 10.3390/molecules27248765. PMID: 36557897; PMCID: PMC9788418.
In vivo protocol: 1. Stevens NC, Edwards PC, Tran LM, Ding X, Van Winkle LS, Fiehn O. Metabolomics of Lung Microdissections Reveals Region- and Sex-Specific Metabolic Effects of Acute Naphthalene Exposure in Mice. Toxicol Sci. 2021 Nov 24;184(2):214-222. doi: 10.1093/toxsci/kfab110. PMID: 34498071; PMCID: PMC8633889. 2. Kovalchuk N, Zhang QY, Van Winkle L, Ding X. Contribution of Pulmonary CYP-mediated Bioactivation of Naphthalene to Airway Epithelial Injury in the Lung. Toxicol Sci. 2020 Oct 1;177(2):334-346. doi: 10.1093/toxsci/kfaa114. PMID: 32974682; PMCID: PMC7548286.

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1: Tam TLD, Ng CK, Lu X, Lim ZL, Wu J. Anion-π interactions of highly π-acidic dipyridinium-naphthalene diimide salts. Chem Commun (Camb). 2018 Jun 18. doi: 10.1039/c8cc03941k. [Epub ahead of print] PubMed PMID: 29911219.

2: Wang X, Wang M, Wang X, Du L, Chu F, Ding W, Gu H, Wang H. A novel naphthalene carboxylic acid-based ionic liquid mixed disperser combined with ultrasonic-enhanced in-situ metathesis reaction for preconcentration of triclosan and methyltriclosan in milk and eggs. Ultrason Sonochem. 2018 Oct;47:57-67. doi: 10.1016/j.ultsonch.2018.04.006. Epub 2018 Apr 26. PubMed PMID: 29908607.

3: Xie X, Wang J, Zheng J, Huang J, Ni C, Cheng J, Hao Z, Ouyang G. Low-cost Scholl-coupling microporous polymer as an efficient solid-phase microextraction coating for the detection of light aromatic compounds. Anal Chim Acta. 2018 Oct 31;1029:30-36. doi: 10.1016/j.aca.2018.05.021. Epub 2018 May 11. PubMed PMID: 29907287.

4: Sun Y, Dong D, Zhang L, He S, Hua X, Guo Z. Polycyclic aromatic hydrocarbons (PAHs) in an urban river at mid and high latitudes: A case study in Siping, a traditional industrial city in Northeast China. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2018 Jun 14:1-8. doi: 10.1080/10934529.2018.1470804. [Epub ahead of print] PubMed PMID: 29902118.

5: Parise JAR, Saboya FEM. Experimental data on transport coefficients for developing laminar flow in isosceles triangular ducts using the naphthalene sublimation technique. Data Brief. 2018 Mar 27;18:1350-1359. doi: 10.1016/j.dib.2018.03.090. eCollection 2018 Jun. PubMed PMID: 29900314; PubMed Central PMCID: PMC5996406.

6: Taublaender MJ, Glöcklhofer F, Marchetti-Deschmann M, Unterlass MM. Green and Rapid Hydrothermal Crystallization and Synthesis of Fully Conjugated Aromatic Compounds. Angew Chem Int Ed Engl. 2018 Jun 13. doi: 10.1002/anie.201801277. [Epub ahead of print] PubMed PMID: 29897647.

7: Shen ML, Xu L, Liu B, Jiao H, Kwon YU. A thermosensitive fluorescent Eu-based metal-organic framework and its polyether sulfone composite film as a thermal sensor. Dalton Trans. 2018 Jun 13. doi: 10.1039/c8dt01690a. [Epub ahead of print] PubMed PMID: 29896598.

8: Jin L, Zhao S, Chen X. Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts. Molecules. 2018 Jun 12;23(6). pii: E1421. doi: 10.3390/molecules23061421. PubMed PMID: 29895754.

9: Duan P, Cao X, Pham H, Datye A, Schmidt-Rohr K. Protective Carbon Overlayers from 2,3-Naphthalenediol Pyrolysis on Mesoporous SiO₂ and Al₂O₃ Analyzed by Solid-State NMR. Materials (Basel). 2018 Jun 9;11(6). pii: E980. doi: 10.3390/ma11060980. PubMed PMID: 29890759.

10: Wu T, Xu J, Xie W, Yao Z, Yang H, Sun C, Li X. Pseudomonas aeruginosa L10: A Hydrocarbon-Degrading, Biosurfactant-Producing, and Plant-Growth-Promoting Endophytic Bacterium Isolated From a Reed (Phragmites australis). Front Microbiol. 2018 May 25;9:1087. doi: 10.3389/fmicb.2018.01087. eCollection 2018. PubMed PMID: 29887849; PubMed Central PMCID: PMC5980988.

11: Dutta K, Shityakov S, Khalifa I, Mal A, Moulik SP, Panda AK, Ghosh C. Effects of secondary carbon supplement on biofilm-mediated biodegradation of naphthalene by mutated naphthalene 1, 2-dioxygenase encoded by Pseudomonas putida strain KD9. J Hazard Mater. 2018 May 18;357:187-197. doi: 10.1016/j.jhazmat.2018.05.024. [Epub ahead of print] PubMed PMID: 29886364.

12: Ren J, Li J, Chen Z, Cheng F. Fate and wetting potential of bio-refractory organics in membrane distillation for coke wastewater treatment. Chemosphere. 2018 Jun 2;208:450-459. doi: 10.1016/j.chemosphere.2018.06.002. [Epub ahead of print] PubMed PMID: 29886333.

13: Deans BJ, Tedone L, Bissember AC, Smith JA. Phytochemical profile of the rare, ancient clone Lomatia tasmanica and comparison to other endemic Tasmanian species L. tinctoria and L. polymorpha. Phytochemistry. 2018 Jun 7;153:74-78. doi: 10.1016/j.phytochem.2018.05.019. [Epub ahead of print] PubMed PMID: 29886159.

14: Nahhas AF, Chang R, Webster TJ. Introducing Unnatural Amino Acids-Containing Tripeptides as Antimicrobial and Anticancer Agents. J Biomed Nanotechnol. 2018 May 1;14(5):987-993. doi: 10.1166/jbn.2018.2555. PubMed PMID: 29883568.

15: Agoun-Bahar S, Djebbar R, Nait Achour T, Abrous-Belbachir O. Soil-to-plant transfer of naphthalene and its effects on seedlings pea (Pisum sativum L.) grown on contaminated soil. Environ Technol. 2018 Jun 13:1-11. doi: 10.1080/09593330.2018.1485752. [Epub ahead of print] PubMed PMID: 29883289.

16: Lv HT, Li HM, Zou GD, Cui Y, Huang Y, Fan Y. Titanium-oxo clusters functionalized with catecholate-type ligands: modulating the optical properties through charge-transfer transitions. Dalton Trans. 2018 Jun 8. doi: 10.1039/c8dt01844h. [Epub ahead of print] PubMed PMID: 29882946.

17: Karaush NN, Minaeva VA, Baryshnikov GV, Minaev BF, Ågren H. Identification of tautomeric intermediates of a novel thiazolylazonaphthol dye - A density functional theory study. Spectrochim Acta A Mol Biomol Spectrosc. 2018 May 29;203:324-332. doi: 10.1016/j.saa.2018.05.096. [Epub ahead of print] PubMed PMID: 29879648.

18: Huang Y, Zeng X, Cao H. Hormonal regulation of floret closure of rice (Oryza sativa). PLoS One. 2018 Jun 7;13(6):e0198828. doi: 10.1371/journal.pone.0198828. eCollection 2018. PubMed PMID: 29879200; PubMed Central PMCID: PMC5991738.

19: Xue J, Zhang L, Qin Z, Li R, Wang Y, Zhu K, Li X, Gao X, Zhang J. No obvious sympathetic excitation after massive levothyroxine overdose: A case report. Medicine (Baltimore). 2018 Jun;97(23):e10909. doi: 10.1097/MD.0000000000010909. PubMed PMID: 29879029.

20: Liu LP, Li Q, Xiang SP, Liu L, Zhong XX, Liang C, Li GH, Hayat T, Alharbi NS, Li FB, Zhu NY, Wong WY, Qin HM, Wang L. Near-saturated red emitters: four-coordinate copper(i) halide complexes containing 8-(diphenylphosphino)quinoline and 1-(diphenylphosphino)naphthalene ligands. Dalton Trans. 2018 Jun 7. doi: 10.1039/c7dt04528j. [Epub ahead of print] PubMed PMID: 29878015.