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M0418

Sigma-Aldrich

Melanin

BioReagent, Synthetic, suitable for cell culture

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About This Item

CAS Number:
8049-97-6
EC Number:
232-473-6
MDL number:
MFCD00131581
UNSPSC Code:
12352209
NACRES:
NA.75

biological source

synthetic

product line

BioReagent

Assay

≥97% (TLC)

form

powder

technique(s)

cell culture | mammalian: suitable

solubility

1 N NH4OH: 20 mg/mL

storage temp.

−20°C

InChI

1S/C18H10N2O4/c1-5-13-9-7(3-19-13)12-10-8(11(9)17(23)15(5)21)4-20-14(10)6(2)16(22)18(12)24/h3-4,19-20H,1-2H3

InChI key

XUMBMVFBXHLACL-UHFFFAOYSA-N

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General description

Melanin is a distinctive class of pigment found in animals, plants, bacteria, and fungi. It is an amorphous polymer formed by the polymerization of phenolic and indolic compounds.

Application

Melanin has been used:
  • to incubate normal human keratinocytes for Masson-Fontana staining
  • as a standard in the determination of melanin content in normal human epidermal melanocytes and immortalized human keratinocytes
  • as an absorber to mimic human skin or melanocytic nevi and melanoma

Biochem/physiol Actions

Melanin plays a role in camouflage and energy harvesting. It also helps in protection against ionizing UV radiations, protection against biotic factors such as host defense against pathogens, and abiotic factors like heat, cold and osmotic stress. Melanin acts as a potent cation chelator and is a component of several photoprotective creams as it facilitates free radical scavenging activity. Melanin may be useful as a photo protectant in cell culture.

Preparation Note

Prepared by oxidation of tyrosine with hydrogen peroxide.

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Michael Waisberg et al.
PloS one, 7(1), e29493-e29493 (2012-01-14)
Malaria has had the largest impact of any infectious disease on shaping the human genome, exerting enormous selective pressure on genes that improve survival in severe malaria infections. Modern humans originated in Africa and lost skin melanization as they migrated
Naira V Margaryan et al.
International journal of molecular sciences, 17(3), 418-418 (2016-03-25)
Expression of Nodal, a Transforming Growth Factor-beta (TGF-β) related growth factor, is associated with aggressive melanoma. Nodal expression in adult dysplastic nevi may predict the development of aggressive melanoma in some patients. A subset of pediatric patients diagnosed with giant
Nadine Santana-Magal et al.
Cancer research, 80(10), 1942-1956 (2020-03-05)
The recent success of checkpoint blockade therapies has established immunotherapy as one of the most promising treatments for melanoma. Nonetheless, a complete curative response following immunotherapy is observed only in a fraction of patients. To identify what factors limit the
Li Ni-Komatsu et al.
Molecular pharmacology, 74(6), 1576-1586 (2008-09-20)
A series of quinolines, including chloroquine and quinine, were identified as potent pigmentation inhibitors through screening a compound library in murine melanocytes. Structure-activity relationship analysis indicated that 4-substituted amino groups with a tertiary amine side chain, such as chloroquine, were

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