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63605

Sigma-Aldrich

α-Melanocyte stimulating hormone

≥97.0% (HPCE/HPLC)

Synonym(s):

α-MSH, α-Melanotropin

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About This Item

Empirical Formula (Hill Notation):
C77H109N21O19S
CAS Number:
581-05-5
Molecular Weight:
1664.88
Beilstein/REAXYS Number:
741840
MDL number:
MFCD00133062
UNSPSC Code:
12352200
PubChem Substance ID:
24882755

assay

≥70% peptide basis
≥97.0% (HPCE/HPLC)

solubility

H2O: 1 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(C)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](Cc2c[nH]cn2)C(=O)N[C@@H](Cc3ccccc3)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc4c[nH]c5ccccc45)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N6CCC[C@H]6C(=O)N[C@@H](C(C)C)C(N)=O

InChI

1S/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83)/t51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,64-/m0/s1

InChI key

WHNFPRLDDSXQCL-UAZQEYIDSA-N

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Amino Acid Sequence

Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2

Biochem/physiol Actions

Pituitary hormone which causes darkening skin pigmentation from amphibians to humans. In mammals, it can also have behavioral effects on learning, attention, and memory.

Antibody Adsorbant

Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2

replaced by

Product No.
Description
Pricing

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCBD2956V
BCBD1273V
BCBD1274V
BCBC1350
BCBC6459

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P C Datta et al.
Neuroscience and biobehavioral reviews, 6(3), 297-310 (1982-01-01)
Melanocyte-stimulating hormone (MSH) has putative adaptive significance in all forms of species where it is present. In mammals the polypeptide chain influences learning, memory and attention. Chemically MSH shares the first 13 (alpha-MSH) or the first 18 or 22 (beta-MSH)
M Baltatzi et al.
International journal of clinical practice, 62(9), 1432-1440 (2008-09-17)
Obesity and hypertension frequently coexist and both represent important risk factors for cardiovascular disease. The mechanisms implicated in the regulation of food intake have not been completely elucidated. Recent data suggests that peripheral and central neuropeptides play an important role
Anaies Nazarians-Armavil et al.
The Journal of endocrinology, 220(1), 13-24 (2013-10-19)
POMC neurons play a central role in the maintenance of whole-body energy homeostasis. This balance requires proper regulation of POMC neurons by metabolic hormones, such as insulin. However, the heterogeneous cellular population of the intact hypothalamus presents challenges for examining
Maurício Morais et al.
Journal of medicinal chemistry, 56(5), 1961-1973 (2013-02-19)
Aiming at the design of specific melanocortin-1 receptor (MC1R) targeted imaging probes, we report on the effect of different azolyl-ring substitution patterns (carboxylate at the 4-position and/or methyl groups at the 3,5 positions) of pyrazolyl-diamine bifunctional chelators (Pz(2)-Pz(4)) on the
Mark E Samuels et al.
The Journal of clinical endocrinology and metabolism, 98(2), 736-742 (2013-01-08)
A 4-year-old girl and a 4-month-old boy presented with hypoglycemia, normal electrolytes, low cortisol, and high ACTH. A diagnosis of primary adrenal insufficiency was made and initial treatment was with glucocorticoids and mineralocorticoids. The genes known to cause ACTH resistance
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