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MedKoo Cat#: 555144 | Name: Defensamide
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Description:

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

Defensamide, also known as MHP and methyl caprooyl tyrosinate, is an activator of sphingosine kinase (SPHK1), and significantly stimulates CAMP mRNA and protein production in KC.

Chemical Structure

Defensamide
Defensamide
CAS#1104874-94-3

Theoretical Analysis

MedKoo Cat#: 555144

Name: Defensamide

CAS#: 1104874-94-3

Chemical Formula: C16H23NO4

Exact Mass: 293.1627

Molecular Weight: 293.36

Elemental Analysis: C, 65.51; H, 7.90; N, 4.77; O, 21.81

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 weeks
100mg USD 750.00 2 weeks
200mg USD 1,250.00 2 weeks
500mg USD 1,950.00 2 weeks
1g USD 2,950.00 2 weeks
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Related CAS #
No Data
Synonym
Defensamide; methyl caprooyl tyrosinate; MHP;
IUPAC/Chemical Name
(S)-Methyl 2-(hexanamido)-3-(4-hydroxyphenyl)propanoate
InChi Key
GBTVWZMJUZJPBU-AWEZNQCLSA-N
InChi Code
InChI=1S/C16H23NO4/c1-3-4-5-6-15(19)17-14(16(20)21-2)11-12-7-9-13(18)10-8-12/h7-10,14,18H,3-6,11H2,1-2H3,(H,17,19)/t14-/m0/s1
SMILES Code
O=C(OC)[C@@H](NC(CCCCC)=O)CC1=CC=C(O)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:
MHP (Methyl caprooyl tyrosinate) is an activator of sphingosine kinase (SPHK1), and significantly stimulates CAMP mRNA and protein production. MHP (Methyl caprooyl tyrosinate) enhances antimicrobial defense and innate immunity.
In vitro activity:
Here, it was investigated whether the next generation of exogenous SPHK1 activator, MHP, also increases cellular S1P levels. Lipid quantification demonstrated that MHP significantly increased S1P levels in human KC (Table 1). Since cellular levels of S1P are tightly regulated not only by SPHK, but also by the S1P degrading enzyme, S1P lyase, it was next assessed whether MHP altered activities of one or both these enzymes. Enzyme activity assays showed that MHP treatment significantly increased SPHK1 activity, but not S1P lyase activity (Table 2). Moreover, the role of SPHK1 on S1P-mediated CAMP stimulation was further assessed by transfecting cells with SPHK1 siRNA. Treatment with MHP increased CAMP protein expression, whereas, CAMP expression was significantly attenuated in cells in which SPHK1 levels were knocked down by siRNA (Fig. 2). Together, these results suggest that MHP activates SPHK1, increasing cellular levels of S1P leading to stimulation of CAMP production. Reference: J Dermatol Sci. 2015 Sep; 79(3): 229–234. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4624019/
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMSO 100.0 340.88
H2O 50.0 170.44
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 293.36 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. Jeong SK, Kim YI, Shin KO, Kim BW, Lee SH, Jeon JE, Kim HJ, Lee YM, Mauro TM, Elias PM, Uchida Y, Park K. Sphingosine kinase 1 activation enhances epidermal innate immunity through sphingosine-1-phosphate stimulation of cathelicidin production. J Dermatol Sci. 2015 Sep;79(3):229-34. doi: 10.1016/j.jdermsci.2015.06.007. Epub 2015 Jun 19. PMID: 26113114; PMCID: PMC4624019.
In vitro protocol:
1. Jeong SK, Kim YI, Shin KO, Kim BW, Lee SH, Jeon JE, Kim HJ, Lee YM, Mauro TM, Elias PM, Uchida Y, Park K. Sphingosine kinase 1 activation enhances epidermal innate immunity through sphingosine-1-phosphate stimulation of cathelicidin production. J Dermatol Sci. 2015 Sep;79(3):229-34. doi: 10.1016/j.jdermsci.2015.06.007. Epub 2015 Jun 19. PMID: 26113114; PMCID: PMC4624019.
In vivo protocol:
TBD