This product is tested for solubility in Ethanol at 50 mg/mL. Melatonin is reportedly soluble at 2 mg/mL in water. Solutions are light sensitive and subject to oxidation. The long term stability of this material in solution has not been determined. Solutions may be stable for up to 2 weeks in a 30:70 solution of isopropanol and water at 0-5°C. Please see the link below to review additional information available in the product datasheet:
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/335/752/m5250pis.pdf
M5250
Melatonin
powder, ≥98% (TLC)
Melatonin
Synonym(s):
N-Acetyl-5-methoxytryptamine
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250 MG
$63.80
1 G
$157.00
5 G
$653.00
10 G
$1,080.00
About This Item
Empirical Formula (Hill Notation):
C13H16N2O2
CAS Number:
Molecular Weight:
232.28
UNSPSC Code:
12352200
NACRES:
NA.32
PubChem Substance ID:
EC Number:
200-797-7
Beilstein/REAXYS Number:
205542
MDL number:
Biological source:
synthetic (organic)
Form:
powder
Assay:
≥98% (TLC)
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Product Name
Melatonin, powder, ≥98% (TLC)
InChI key
DRLFMBDRBRZALE-UHFFFAOYSA-N
InChI
1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
SMILES string
COc1ccc2[nH]cc(CCNC(C)=O)c2c1
biological source
synthetic (organic)
assay
≥98% (TLC)
form
powder
color
white to off-white
mp
116.5-118 °C (lit.)
solubility
ethanol: 50 mg/mL
storage temp.
−20°C
Quality Level
Gene Information
human ... MTNR1A(4543), MTNR1B(4544), NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)
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This Item | PHL22330 | 1380105 | BP1077 |
|---|---|---|---|
| biological source synthetic (organic) | biological source - | biological source - | biological source - |
| assay ≥98% (TLC) | assay ≥95.0% (HPLC) | assay - | assay - |
| Quality Level 200 | Quality Level - | Quality Level - | Quality Level - |
| form powder | form - | form - | form crystalline |
| storage temp. −20°C | storage temp. 2-8°C | storage temp. 2-8°C | storage temp. 2-8°C |
| Gene Information human ... MTNR1A(4543), MTNR1B(4544), NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846) | Gene Information - | Gene Information - | Gene Information - |
Application
Melatonin has been administered to experimental animals for following studies:
- To determine if long-term melatonin administration is able to induce reproductive changes and how melatonin exerts its protective action related to lipid oxidation and antioxidant activities in the rat ovary during ovulation.[1]
- To determine the effect of melatonin on endoplasmic reticulum stress and sirtuin 1 expression in neuronal cells of newborn rats after hypoxia–ischemia.[2]
- To study the effect of melatonin on chronic stress-induced gut dysfunction in stressed mice.[3]
Biochem/physiol Actions
Hormone; mediates photoperiodicity in mammals; inhibits cerebellar nitric oxide synthetase; peroxynitrite scavenger. Melatonin has complex effects on apoptotic pathways, inhibiting apoptosis in immune cells and neurons but enhancing apoptotic cell death of cancer cells. Inhibits proliferation/metastasis of breast cancer cells by inhibiting estrogen receptor action.
Melatonin is characterized with variety of properties such as antioxidant, autocoid, paracoid and hormonal properties, as well as anti- inflammatory and anti-apoptotic properties.[4] Melatonin is implicated in the regulation of seasonal reproduction, energy metabolism and thermoregulation in mammals.[1] Melatonin plays a vital role in the lessening of neonatal hypoxia–ischemia (HI) induced endoplasmic reticulum (ER) stress and conserves sirtuin 1( SIRT-1) expression.[2]
Disclaimer
Solutions are light sensitive and subject to oxidation.
General description
Melatonin (N-acetyl-5-methoxytryptamine) is synthesized from an essential amino acid tryptophan. It is a pineal gland neurohormone.[3][4] Direct, non-receptor-mediated free radical scavenging activity induced by melatonin, makes it unique from other classic hormones. Melatonin is expressed in variety of organisms such as bacteria, algae, fungi, plants, insects, and vertebrates including humans.[4][2]
Other Notes
This product is not tested for cell culture. End users must qualify this product for their respective applications.
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Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Melatonin: a hormone, a tissue factor, an autocoid, a paracoid, and an antioxidant vitamin.
Tan DX
Journal of Pineal Research, 34(1), 75-78 (2003)
Melatonin attenuates stress-induced defecation: lesson from a rat model of stress-induced gut dysfunction.
Song GH
Neurogastroenterology and Motility, 17(5), 744-750 (2005)
Long-term melatonin treatment reduces ovarian mass and enhances tissue antioxidant defenses during ovulation in the rat.
Chuffa LG
Brazilian journal of medical and biological research, 44(3), 217-223 (2011)
Song Ding et al.
Journal of pineal research, 67(2), e12581-e12581 (2019-04-23)
Rupture of vulnerable plaques is the main trigger of acute cardio-cerebral vascular events, but mechanisms responsible for transforming a stable atherosclerotic into a vulnerable plaque remain largely unknown. Melatonin, an indoleamine hormone secreted by the pineal gland, plays pleiotropic roles
Silvia Rivara et al.
Journal of medicinal chemistry, 50(26), 6618-6626 (2007-12-07)
A novel series of melatonin receptor ligands, characterized by a N-(substituted-anilinoethyl)amido scaffold, along with preliminary structure-activity relationships (SARs), is presented. MT1 and MT2 receptor binding affinity and intrinsic activity have been modulated by the introduction of different substituents on the
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HOW TO MAKE A STOCK SOLUTION ?
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What is the recommended method for storing stock solutions of item M5250, Melatonin?
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Following reconstitution for item M5250, Melatonin, it is recommended to aliquot and freeze it at -20°C. Stock solutions are stable for up to 3 months at -20°C.
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What is the shelf-life of this product when stored at -20C?
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This product is not assigned an expiration date or recommended retest date. Products with no expiration date or recommended retest date should be routinely inspected by customers to ensure they perform as expected. These products are also subject to a one year warranty from the date of shipment. For more information you may access the "Product Dating Information" document under "ADDITIONAL USEFUL DOCUMENTS ABOUT OUR PRODUCTS" at the bottom of the Quality Services page with this link: https://www.sigmaaldrich.com/life-science/quality-and-regulatory-management/quality-services.
Please see the link below to the product information sheet for additional product information.
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/335/752/m5250pis.pdfHelpful?
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Can I use melatonin for cell culture?
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This product is not tested for cell culture. End users must qualify this product for their respective applications.
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