| Size | Price | Stock | Qty |
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| 500mg |
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| 5g |
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| Other Sizes |
| Targets |
The aglycone Raspberry ketone glucoside (after conversion to raspberry ketone) targets nitric oxide (NO) with a scavenging effect (at 0.01×10⁻⁴ M, ratio of NO signal intensity 0.3 vs control 1.0; the glucoside itself showed little NO scavenging at the same concentration, ratio 0.9). It also targets superoxide anion (O₂⁻) and lipid peroxidation. Additionally, it suppresses tyrosinase activation induced by NO in normal human melanocytes. [1]
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| ln Vitro |
Raspberry ketone glucoside (3×10⁻⁵ M) significantly inhibited melanin synthesis in B16 melanoma cells after 72 h culture, showing a stronger effect than arbutin (Fig.-1). [1]
Among various glycosides, only the glucoside form of raspberry ketone exhibited high melanin synthesis inhibition; other sugar moieties (different glycosides) showed no significant effect (Fig.-2). [1] p-Alkyl phenyl glucosides with alkyl chain length of C4 (butylphenyl glucoside) maintained high inhibitory effect on melanin synthesis without suppressing cell proliferation; longer chains (C6) caused cytotoxicity (Fig.-3). [1] The aglycone raspberry ketone (released from Raspberry ketone glucoside) showed higher melanin synthesis inhibition than the glucoside itself in B16 melanoma cells (Fig.-6). [1] Raspberry ketone (0.01×10⁻⁴ M) exhibited a remarkable nitric oxide (NO) scavenging effect as measured by ESR (Table-1). [1] Raspberry ketone (concentrations not specified as IC₅₀, but shown concentration-dependently) significantly suppressed the increase of tyrosinase activity stimulated by the NO donor SNAP (200 μM) in normal human melanocytes (Fig.-7). [1] Raspberry ketone showed superoxide anion (O₂⁻) scavenging activity in a concentration-dependent manner (Fig.-8, using xanthine/xanthine oxidase/NBT system). [1] Raspberry ketone also inhibited lipid peroxide generation in a concentration-dependent manner (Fig.-9, using methyl linoleate/hypoxanthine/xanthine oxidase/TBA method). [1] |
| Enzyme Assay |
For nitric oxide (NO) scavenging assay, Raspberry ketone glucoside and its aglycone raspberry ketone were tested using ESR spectroscopy. NOC 7 was used as an NO donor, and carboxyl-PTIO as a spin-trapping agent. The NO signal intensity was expressed as a ratio relative to control. At a concentration of 0.01×10⁻⁴ M, raspberry ketone reduced the NO signal to 0.3 of control, while Raspberry ketone glucoside only reduced it to 0.9 (Table-1). [1]
For superoxide anion (O₂⁻) scavenging assay, the xanthine/xanthine oxidase system was employed. The reaction mixture contained 0.05 M sodium carbonate buffer (pH 10.2), 3 mM xanthine, 3 mM EDTA, 0.15% bovine serum albumin, 0.75 mM nitroblue tetrazolium (NBT), and various concentrations of raspberry ketone. After preincubation at 25°C for 10 min, diluted xanthine oxidase from buttermilk was added and the mixture was incubated at 25°C for 20 min. The reaction was stopped by adding 6 mM copper chloride, and absorbance at 560 nm was measured. The inhibition percentage was calculated relative to control (water instead of sample). A concentration-dependent O₂⁻ scavenging effect was observed (Fig.-8). [1] For lipid peroxide inhibition assay, methyl linoleate, 1 mM hypoxanthine (containing 0.1% Triton X-100), and various concentrations of raspberry ketone were mixed. Then diluted xanthine oxidase from buttermilk was added and the mixture was shaken at 37°C for 24 h. After reaction, 10% phosphotungstic acid and 0.67% thiobarbituric acid (TBA) were added, stirred, and heated at 95–100°C for 30 min. The mixture was rapidly cooled, n-butanol was added, shaken, and centrifuged at 3,000 rpm for 10 min. Absorbance of the supernatant was measured at 535 nm. The inhibition percentage was calculated relative to control. A concentration-dependent inhibition of lipid peroxide generation was observed (Fig.-9). [1] |
| Cell Assay |
B16 melanoma cells (3×10⁵ cells/90 mm dish) were treated with various glycosides including Raspberry ketone glucoside at 3×10⁻⁵ M for 72 h. After culture, cells were trypsinized, centrifuged, and sequentially treated with 5% TCA, ethanol:diethyl ether (3:1), and ether. Cells were then dissolved in Soluene-350, and absorbance at 400 nm was measured using a spectrophotometer. Melanin synthesis inhibition was determined compared to non-treated control (Fig.-1, -2, -3). [1]
For the degradation study, homogenates of human stratum corneum (from heel) and desquamated stratum corneum cells (obtained after 4-day culture in buffer pH 5.0) were incubated with 0.1% Raspberry ketone glucoside at 37°C in pH 5.0 buffer. The amount of released aglycone (raspberry ketone) was analyzed by HPLC (UV 280 nm, ODS column, eluent methanol:water=2:8). Time-dependent generation of raspberry ketone was confirmed (Fig.-4, -5). [1] Normal human melanocytes (6×10⁵ cells/well in 24-well collagen type I plate) were preincubated with various concentrations of raspberry ketone for 24 h, then stimulated with 200 μM NO donor SNAP for 72 h. 18 h before termination, 1.0 μCi/well of ³H-tyrosine was added. Cells were then treated with 10% TCA containing 20% activated charcoal, and the amount of released ³H₂O in the supernatant was measured to determine tyrosinase activity. Raspberry ketone showed a concentration-dependent suppression of NO-stimulated tyrosinase activation (Fig.-7). [1] |
| ADME/Pharmacokinetics |
Raspberry ketone glucoside is degraded by human stratum corneum homogenates and desquamated stratum corneum cells, releasing its aglycone raspberry ketone over time (Fig.-4, -5). This degradation is likely mediated by β-glucosidase present in human epidermis. The glucoside is water-soluble, odorless, and stable, which are favorable properties for formulation. Upon application to skin, it gradually converts to raspberry ketone, providing sustained melanogenesis inhibition. [1]
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| Toxicity/Toxicokinetics |
The aglycone raspberry ketone (derived from Raspberry ketone glucoside) has been reported to have high safety in humans (reference 25 cited). No specific toxicity data (e.g., LD₅₀, hepatotoxicity, protein binding) are provided in this paper. [1]
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| References | |
| Additional Infomation |
According to reports, rhubarb, Scots pine, and other organisms with available data contain raspberry ketone glucoside.
Raspberry ketone glucoside is a phenolic glycoside from raspberry fruit. Its aglycone, raspberry ketone, has a strong raspberry odor, making it less suitable for direct cosmetic formulation, whereas the glucoside is odorless and water-soluble. The sustained whitening effect is attributed to the gradual enzymatic release of raspberry ketone in the skin, which not only inhibits melanin synthesis but also scavenges nitric oxide (NO), superoxide anion, and inhibits lipid peroxidation—factors involved in UV-induced pigmentation. The structure-activity relationship suggests that a glucose sugar moiety and an alkyl chain length of C4 (as in raspberry ketone) are optimal for melanogenesis inhibition without cytotoxicity. This compound is proposed as a new type of lasting whitening active ingredient with high stability, safety, and water solubility. [1] |
| Molecular Formula |
C16H22O7
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|---|---|
| Molecular Weight |
326.3417
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| Exact Mass |
326.136
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| CAS # |
38963-94-9
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| PubChem CID |
5320521
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| Appearance |
White to off-white solid
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
553.8±50.0 °C at 760 mmHg
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| Flash Point |
202.8±23.6 °C
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| Vapour Pressure |
0.0±1.6 mmHg at 25°C
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| Index of Refraction |
1.590
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| LogP |
-1.22
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
23
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| Complexity |
381
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| Defined Atom Stereocenter Count |
5
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| SMILES |
O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1C([H])=C([H])C(=C([H])C=1[H])C([H])([H])C([H])([H])C(C([H])([H])[H])=O
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| InChi Key |
IDONYWHRKBUDOR-IBEHDNSVSA-N
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| InChi Code |
InChI=1S/C16H22O7/c1-9(18)2-3-10-4-6-11(7-5-10)22-16-15(21)14(20)13(19)12(8-17)23-16/h4-7,12-17,19-21H,2-3,8H2,1H3/t12-,13-,14+,15-,16-/m1/s1
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| Chemical Name |
4-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]butan-2-one
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~153.21 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.66 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.66 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. View More
Solubility in Formulation 3: ≥ 1.72 mg/mL (5.27 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0643 mL | 15.3214 mL | 30.6429 mL | |
| 5 mM | 0.6129 mL | 3.0643 mL | 6.1286 mL | |
| 10 mM | 0.3064 mL | 1.5321 mL | 3.0643 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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