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MedKoo Cat#: 328604 | Name: Monobenzone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Monobenzone, also known as Benoquin, is a tyrosinase inhibitor used to treat vitiligo by depigmentation. Monobenzone may cause destruction of melanocytes.

Chemical Structure

Monobenzone
Monobenzone
CAS#103-16-2

Theoretical Analysis

MedKoo Cat#: 328604

Name: Monobenzone

CAS#: 103-16-2

Chemical Formula: C13H12O2

Exact Mass: 200.0837

Molecular Weight: 200.24

Elemental Analysis: C, 77.98; H, 6.04; O, 15.98

Price and Availability

Size Price Availability Quantity
25g USD 190.00
100g USD 360.00
500g USD 800.00
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Related CAS #
No Data
Synonym
Monobenzone; Benoquin; AI3-14325; AI3 14325; AI314325; BRN 1958305; BRN-1958305; BRN1958305
IUPAC/Chemical Name
4-(benzyloxy)phenol
InChi Key
VYQNWZOUAUKGHI-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2
SMILES Code
OC1=CC=C(OCC2=CC=CC=C2)C=C1
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
View handling instruction
Biological target:
Monobenzone is a potent skin depigmenting agent.
In vitro activity:
Further cellular study confirmed that monobenzone could inhibit the proliferation of gastric cancer cell lines MGC-803 and BGC-823 with IC50 as 7.82 ± 0.55 μM and 6.99 ± 0.51 μM, respectively, and erase the substrate of KDM1A, H3K4me1/2 and H3K9 me2, and inhibit the migration of gastric cancer cell by reversing epithelial-mesenchymal transition (EMT). Reference: Front Pharmacol. 2021 Apr 15;12:640949. https://pubmed.ncbi.nlm.nih.gov/33935733/
In vivo activity:
This study developed a new mouse model of vitiligo by topically applying the skin-depigmenting agent monobenzone on mice. This study demonstrated that monobenzone-induced skin depigmentation on the non-exposed sites and that the severity of lesions depended on drug dosage. The result of the histological examination of the depigmented skin indicated loss of epidermal melanocytes and perilesional accumulation of CD8⁺ T cells. Furthermore, the monobenzone-induced depigmentation of the Rag1 gene knockout did not appear on the non-exposed sites, supporting the involvement of infiltrating CD8⁺ T cells in melanocyte destruction. Reference: Cancers (Basel). 2022 Sep 27;14(19):4710. https://pubmed.ncbi.nlm.nih.gov/36230632/
Solvent mg/mL mM
Solubility
DMSO 70.0 349.59
Ethanol 40.0 199.76
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 200.24 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. Ma P, Jia G, Song Z. Monobenzone, a Novel and Potent KDM1A Inhibitor, Suppresses Migration of Gastric Cancer Cells. Front Pharmacol. 2021 Apr 15;12:640949. doi: 10.3389/fphar.2021.640949. PMID: 33935733; PMCID: PMC8084583. 2. van den Boorn JG, Picavet DI, van Swieten PF, van Veen HA, Konijnenberg D, van Veelen PA, van Capel T, Jong EC, Reits EA, Drijfhout JW, Bos JD, Melief CJ, Luiten RM. Skin-depigmenting agent monobenzone induces potent T-cell autoimmunity toward pigmented cells by tyrosinase haptenation and melanosome autophagy. J Invest Dermatol. 2011 Jun;131(6):1240-51. doi: 10.1038/jid.2011.16. Epub 2011 Feb 17. PMID: 21326294. 3. Dong J, Zhong T, Xu Z, Chen H, Wang X, Yang L, Lou Z, Xu Y, Hou T, Xu R, Zhu W, Shao J. Identification of Monobenzone as a Novel Potential Anti-Acute Myeloid Leukaemia Agent That Inhibits RNR and Suppresses Tumour Growth in Mouse Xenograft Model. Cancers (Basel). 2022 Sep 27;14(19):4710. doi: 10.3390/cancers14194710. PMID: 36230632; PMCID: PMC9564123. 4. Zhu Y, Wang S, Xu A. A mouse model of vitiligo induced by monobenzone. Exp Dermatol. 2013 Jul;22(7):499-501. doi: 10.1111/exd.12184. PMID: 23800067.
In vitro protocol:
1. Ma P, Jia G, Song Z. Monobenzone, a Novel and Potent KDM1A Inhibitor, Suppresses Migration of Gastric Cancer Cells. Front Pharmacol. 2021 Apr 15;12:640949. doi: 10.3389/fphar.2021.640949. PMID: 33935733; PMCID: PMC8084583. 2. van den Boorn JG, Picavet DI, van Swieten PF, van Veen HA, Konijnenberg D, van Veelen PA, van Capel T, Jong EC, Reits EA, Drijfhout JW, Bos JD, Melief CJ, Luiten RM. Skin-depigmenting agent monobenzone induces potent T-cell autoimmunity toward pigmented cells by tyrosinase haptenation and melanosome autophagy. J Invest Dermatol. 2011 Jun;131(6):1240-51. doi: 10.1038/jid.2011.16. Epub 2011 Feb 17. PMID: 21326294.
In vivo protocol:
1. Dong J, Zhong T, Xu Z, Chen H, Wang X, Yang L, Lou Z, Xu Y, Hou T, Xu R, Zhu W, Shao J. Identification of Monobenzone as a Novel Potential Anti-Acute Myeloid Leukaemia Agent That Inhibits RNR and Suppresses Tumour Growth in Mouse Xenograft Model. Cancers (Basel). 2022 Sep 27;14(19):4710. doi: 10.3390/cancers14194710. PMID: 36230632; PMCID: PMC9564123. 2. Zhu Y, Wang S, Xu A. A mouse model of vitiligo induced by monobenzone. Exp Dermatol. 2013 Jul;22(7):499-501. doi: 10.1111/exd.12184. PMID: 23800067.
1: Zhu Y, Wang S, Xu A. A mouse model of vitiligo induced by monobenzone. Exp Dermatol. 2013 Jul;22(7):499-501. doi: 10.1111/exd.12184. PubMed PMID: 23800067. 2: Lee CS, Joo YH, Baek HS, Park M, Kim JH, Shin HJ, Park NH, Lee JH, Park YH, Shin SS, Lee HK. Different effects of five depigmentary compounds, rhododendrol, raspberry ketone, monobenzone, rucinol and AP736 on melanogenesis and viability of human epidermal melanocytes. Exp Dermatol. 2016 Jan;25(1):44-9. doi: 10.1111/exd.12871. Epub 2015 Nov 23. PubMed PMID: 26440747. 3: van den Boorn JG, Melief CJ, Luiten RM. Monobenzone-induced depigmentation: from enzymatic blockade to autoimmunity. Pigment Cell Melanoma Res. 2011 Aug;24(4):673-9. doi: 10.1111/j.1755-148X.2011.00878.x. Epub 2011 Jul 6. Review. PubMed PMID: 21689385. 4: Rordam OM, Lenouvel EW, Maalo M. Successful treatment of extensive vitiligo with monobenzone. J Clin Aesthet Dermatol. 2012 Dec;5(12):36-9. PubMed PMID: 23277803; PubMed Central PMCID: PMC3533321. 5: van den Boorn JG, Picavet DI, van Swieten PF, van Veen HA, Konijnenberg D, van Veelen PA, van Capel T, Jong EC, Reits EA, Drijfhout JW, Bos JD, Melief CJ, Luiten RM. Skin-depigmenting agent monobenzone induces potent T-cell autoimmunity toward pigmented cells by tyrosinase haptenation and melanosome autophagy. J Invest Dermatol. 2011 Jun;131(6):1240-51. doi: 10.1038/jid.2011.16. Epub 2011 Feb 17. PubMed PMID: 21326294. 6: van den Boorn JG, Jakobs C, Hagen C, Renn M, Luiten RM, Melief CJ, Tüting T, Garbi N, Hartmann G, Hornung V. Inflammasome-Dependent Induction of Adaptive NK Cell Memory. Immunity. 2016 Jun 21;44(6):1406-21. doi: 10.1016/j.immuni.2016.05.008. Epub 2016 Jun 7. PubMed PMID: 27287410. 7: Moreira CG, Carrenho LZ, Pawloski PL, Soley BS, Cabrini DA, Otuki MF. Pre-clinical evidences of Pyrostegia venusta in the treatment of vitiligo. J Ethnopharmacol. 2015 Jun 20;168:315-25. doi: 10.1016/j.jep.2015.03.080. Epub 2015 Apr 8. PubMed PMID: 25862965. 8: Zhu Y, Wang S, Lin F, Li Q, Xu A. The therapeutic effects of EGCG on vitiligo. Fitoterapia. 2014 Dec;99:243-51. doi: 10.1016/j.fitote.2014.08.007. Epub 2014 Aug 12. PubMed PMID: 25128425. 9: van den Boorn JG, Konijnenberg D, Tjin EP, Picavet DI, Meeuwenoord NJ, Filippov DV, van der Veen JP, Bos JD, Melief CJ, Luiten RM. Effective melanoma immunotherapy in mice by the skin-depigmenting agent monobenzone and the adjuvants imiquimod and CpG. PLoS One. 2010 May 13;5(5):e10626. doi: 10.1371/journal.pone.0010626. PubMed PMID: 20498710; PubMed Central PMCID: PMC2869359. 10: Hedges TR 3rd, Kenyon KR, Hanninen LA, Mosher DB. Corneal and conjunctival effects of monobenzone in patients with vitiligo. Arch Ophthalmol. 1983 Jan;101(1):64-8. PubMed PMID: 6849655. 11: Webb KC, Eby JM, Hariharan V, Hernandez C, Luiten RM, Le Poole IC. Enhanced bleaching treatment: opportunities for immune-assisted melanocyte suicide in vitiligo. Exp Dermatol. 2014 Aug;23(8):529-33. doi: 10.1111/exd.12449. Epub 2014 Jul 10. PubMed PMID: 24840876; PubMed Central PMCID: PMC4126600. 12: Catona A, Lanzer D. Monobenzone, Superfade, vitiligo and confetti-like depigmentation. Med J Aust. 1987 Mar 16;146(6):320-1. PubMed PMID: 3821640. 13: Nordlund JJ, Forget B, Kirkwood J, Lerner AB. Dermatitis produced by applications of monobenzone in patients with active vitiligo. Arch Dermatol. 1985 Sep;121(9):1141-4. PubMed PMID: 2931053. 14: BECKER SW Jr, SPENCER MC. Evaluation of monobenzone. JAMA. 1962 Apr 28;180:279-84. PubMed PMID: 13866366. 15: Lubowe IL, Morse JL, Gonzales V. Diffuse leukoderma following use of monobenzone. Arch Dermatol. 1965 Aug;92(2):211-2. PubMed PMID: 11850935.