IUPAC/Chemical Name
4-[(tetrahydro-2H-pyran-2-yl)oxy]-phenol
InChi Key
GFBCWCDNXDKFRH-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H14O3/c12-9-4-6-10(7-5-9)14-11-3-1-2-8-13-11/h4-7,11-12H,1-3,8H2
SMILES Code
OC1=CC=C(OC2OCCCC2)C=C1
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
>3 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
Biological target:
Deoxyarbutin is a new effective lighten ingredient, can effectively inhibit tyrosinase activity and melanin synthesis to get significant and lasting lightening effect.
In vitro activity:
dA (Deoxyarbutin), and its second-generation derivatives dF, fdA, and tdA, exhibit dose-dependent reductions in melanocyte cell number, primarily due to inhibition of proliferation rather than initiation of apoptosis as exemplified by hydroquinone (HQ), ie, cytostatic as opposed to cytotoxic.
Reference: J Drugs Dermatol. 2012 Oct;11(10):e28-34. https://pubmed.ncbi.nlm.nih.gov/23134995/
In vivo activity:
Here, this study further validated the in vivo activity against tumour by a subcutaneously grafted murine melanoma model. As shown in Fig. 5a,b, the average tumour size in the dA (deoxyarbutin)-and 5-Fluorouracil (5-FU) treated groups were 494.91 ± 114.10 and 720.90 ± 31.32 mm3 respectively. Whereas the average tumour size in the model group was 1122.91 ± 284.13 mm3. The results indicated that treatment of dA decreased tumour volumes more effective than 5-FU did.
Reference: Sci Rep. 2017; 7: 7197. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5543205/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
49.7 |
255.73 |
| DMF |
10.0 |
51.49 |
| Ethanol |
32.0 |
164.75 |
| Ethanol:PBS (pH 7.2) (1:20) |
0.0 |
0.21 |
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
194.23
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.
| 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 L, Xu Y, Wei Z, Xin G, Xing Z, Niu H, Huang W. Deoxyarbutin displays antitumour activity against melanoma in vitro and in vivo through a p38-mediated mitochondria associated apoptotic pathway. Sci Rep. 2017 Aug 3;7(1):7197. doi: 10.1038/s41598-017-05416-8. PMID: 28775302; PMCID: PMC5543205.
2. Chawla S, Kvalnes K, deLong MA, Wickett R, Manga P, Boissy RE. DeoxyArbutin and its derivatives inhibit tyrosinase activity and melanin synthesis without inducing reactive oxygen species or apoptosis. J Drugs Dermatol. 2012 Oct;11(10):e28-34. PMID: 23134995.
In vitro protocol:
1. Ma L, Xu Y, Wei Z, Xin G, Xing Z, Niu H, Huang W. Deoxyarbutin displays antitumour activity against melanoma in vitro and in vivo through a p38-mediated mitochondria associated apoptotic pathway. Sci Rep. 2017 Aug 3;7(1):7197. doi: 10.1038/s41598-017-05416-8. PMID: 28775302; PMCID: PMC5543205.
2. Chawla S, Kvalnes K, deLong MA, Wickett R, Manga P, Boissy RE. DeoxyArbutin and its derivatives inhibit tyrosinase activity and melanin synthesis without inducing reactive oxygen species or apoptosis. J Drugs Dermatol. 2012 Oct;11(10):e28-34. PMID: 23134995.
In vivo protocol:
1. Ma L, Xu Y, Wei Z, Xin G, Xing Z, Niu H, Huang W. Deoxyarbutin displays antitumour activity against melanoma in vitro and in vivo through a p38-mediated mitochondria associated apoptotic pathway. Sci Rep. 2017 Aug 3;7(1):7197. doi: 10.1038/s41598-017-05416-8. PMID: 28775302; PMCID: PMC5543205.
1. Chawla, S., deLong, M.A., Visscher, M.O., et al. Mechanism of tyrosinase inhibition by deoxyArbutin and its second-generation derivatives. Br. J. Dermatol. 159(6), 1267-1274 (2008).
2. Hamed, S.H., Sriwiriyanont, P., deLong, M.A., et al. Comparative efficacy and safety of deoxyarbutin, a new tyrosinase-inhibiting agent. J. Cosmet. Sci. 57(4), 291-308 (2006).
3. Ma, L., Xu, Y., Wei, Z., et al. Deoxyarbutin displays antitumour activity against melanoma in vitro and in vivo through a p38-mediated mitochondria associated apoptotic pathway. Sci. Rep. 7(1), 7197 (2017).
