3-O-Ethyl-L-ascorbic acid
(Synonyms: 3-O-乙基抗坏血酸醚；维生素C乙基醚；VC乙基醚；) 目录号 : GC61717
A tyrosinase inhibitor
Cas No.:86404-04-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3-O-ethyl-L-Ascorbic acid is an inhibitor of tyrosinase (IC50s = 16.65 and 29.69 mM for the human and mushroom enzymes, respectively).1,2 It also scavenges DPPH radicals (IC50 = 0.032 g/L).2 Formulations containing 3-O-ethyl-L-ascorbic acid have been used in cosmetic products as skin-lightening agents.
1.Jeon, S.-H., Kim, K.-H., Koh, J.-U., et al.Inhibitory effects on L-dopa oxidation of tyrosinase by skin-whitening agentsBull. Korean Chem. Soc.26(7)1135-1137(2005) 2.Liao, W.C., Huang, Y.-T., Lu, L.-P., et al.Antioxidant ability and stability studies of 3-O-ethyl ascorbic acid, a cosmetic tyrosinase inhibitorJ. Cosmet. Sci.69(4)233-243(2018)
| Cas No. | 86404-04-8 | SDF | |
| 别名 | 3-O-乙基抗坏血酸醚；维生素C乙基醚；VC乙基醚； | ||
| Canonical SMILES | O[C@@H](CO)[C@](O1)([H])C(OCC)=C(O)C1=O | ||
| 分子式 | C8H12O6 | 分子量 | 204.18 |
| 溶解度 | H2O : 100 mg/mL (489.76 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.8976 mL | 24.4882 mL | 48.9764 mL |
| 5 mM | 0.9795 mL | 4.8976 mL | 9.7953 mL |
| 10 mM | 0.4898 mL | 2.4488 mL | 4.8976 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The Anti-Ageing and Whitening Potential of a Cosmetic Serum Containing 3- O-ethyl-l-ascorbic Acid
Life (Basel) 2021 Apr 29;11(5):406.PMID:33946734DOI:10.3390/life11050406.
Skin ageing has many manifestations such as wrinkles, dryness, hyperpigmentation, and uneven skin tone. Extrinsic and intrinsic factors, especially solar ultraviolet light (UVB), contribute to skin ageing; its main features are brown spots, alterations in melanin pigmentation, and a decrease in collagen and hyaluronic acid linked to oxidative stress. Several studies showed that topical products containing ingredients with antioxidant activity can reduce oxidative damage; to provide a maximum anti-ageing effect to the skin, topical products can combine various ingredients. C-SHOT SERUM contains a combination of two molecules with a proven anti-ageing activity: a high percentage (30%) of a more stable vitamin C derivative, 3-O-Ethyl-L-ascorbic acid, and lactic acid (1%). The product showed a high biocompatibility, assessed through an MTT assay on keratinocytes and on Reconstructed Human Epidermis (RHE, SkinEthic); the anti-ageing activity was demonstrated on human dermal fibroblasts and keratinocytes by a statistically significant increase in collagen production and a reduction of a UVB-induced DNA damage marker (γ-H2AX histone), indicating DNA protection. Moreover, a depigmenting activity, shown by a highly significant decrease in melanin content on treated Reconstructed Human Pigmented Epidermis (RHPE), was assessed. According to the data of our study, the tested product contrasts the effect of skin ageing and irregular pigmentation due to the physiological decline of the skin.
3-O-Ethyl-L-ascorbic acid
Acta Crystallogr Sect E Struct Rep Online 2008 Apr 16;64(Pt 5):o860.PMID:21202347DOI:10.1107/S1600536808009963.
In the crystal structure of the title compound, C(8)H(12)O(6), mol-ecules are linked to each other by O-H⋯O hydrogen bonding.
3- O-Ethyl-L-Ascorbic Acid Doped Enteric-Coated Gelatin Capsules towards the Advanced Oral Curcumin Delivery for Cancers
Polymers (Basel) 2022 May 29;14(11):2207.PMID:35683880DOI:10.3390/polym14112207.
Among plant-derived polyphenols, curcumin has been recognized as a therapeutically potent nutrient presenting pleiotropic pharmacological effects on various cancers. However, the poor absorption and bioavailability of curcumin limit the use of this excellent naturally occurring polyphenol. 3-O-Ethyl-L-ascorbic acid (EA) doped enteric-coated gelatin capsules were studied in the search for advanced oral curcumin delivery. The EA doped enteric-coated gelatin capsules were successfully created based on a developed inner dual enteric coating technique. When placed in four buffer solutions with different pHs (pH 2.0, 5.0, 6.0, and 7.3), the coated gelatin capsules showed delayed-release profiles of curcumin below pH 6.0. In contrast, both pristine and fabricated gelatin capsules showed similar curcumin release profiles at pH 7.3, which is a common pH observed in the lower gastrointestinal tract, especially intestinal regions. In conclusion, these results demonstrated the potential of the EA doped enteric-coated gelatin capsules in developing advanced oral delivery of curcumin targeting intestinal-specific regions.
3-O-Ethyl-L-ascorbic acid: Characterisation and investigation of single solvent systems for delivery to the skin
Int J Pharm X 2019 Jul 19;1:100025.PMID:31517290DOI:10.1016/j.ijpx.2019.100025.
l-ascorbic acid (AA), commonly known as vitamin C, has been widely used in topical formulations for many years as an antioxidant and anti-aging ingredient. However, the physicochemical properties of AA are not optimal for skin uptake and the molecule is also unstable, readily undergoing oxidation on exposure to air. The compound 3-O-Ethyl-L-ascorbic acid (EA) has been developed as a stable vitamin C derivative and has been used in topical products. The aims of this work were to conduct a comprehensive characterisation of physicochemical properties of EA as well as to investigate the influence of various neat solvents on EA skin delivery. Nuclear magnetic resonance (NMR), mass spectroscopy, differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) were used to characterise the molecule. The pKa of the compound and the partition coefficient logP(o/w) were experimentally determined. A new HPLC method for analysis of the molecule was also developed and validated. A number of solvents for topical preparations were selected based on their wide use as excipients in topical formulations, their potential to act as skin penetration enhancers and their favourable safety profiles. The solubility and stability of EA was examined. Skin permeation of the molecule in full thickness porcine skin in vitro was investigated using Franz-type diffusion cells. The melting point, log P(o/w) value and pKa value of EA were determined to be 114.39 ± 0.5 °C, -1.07 ± 0.03 and 7.72 ± 0.01 respectively. Skin penetration of EA was evident for the following vehicles 1,2 hexanediol (HEX), glycerol (GLY), propylene glycol (PG), 1,2 pentanediol (1-2P), isopropyl alcohol (IPA), propylene glycol monolaurate (PGML) and propylene glycol monocaprylate (PGMC). Skin uptake but no permeation through the skin was observed for Transcutol® (TC) and dipropylene glycol (DiPG), while no penetration was observed for the solvents 1,5 pentanediol (1-5P) and tripropylene glycol (TriPG). The findings of the permeation experiments confirm the potential of simple formulations to deliver EA to the skin. Studies are ongoing to identify complex vehicles for synergistic enhancement of EA skin penetration. To our knowledge this is the first study to conduct a comprehensive characterization of EA and examine its skin uptake and permeation properties in porcine skin.
Suppression of riboflavin-sensitized singlet oxygen generation by l-ascorbic acid, 3-O-Ethyl-L-ascorbic acid and Trolox
J Photochem Photobiol B 2019 Feb;191:116-122.PMID:30605891DOI:10.1016/j.jphotobiol.2018.12.012.
Riboflavin (RF), a water-soluble vitamin B2, is an endogenous singlet oxygen photosensitizer in human skin and eye. Time profiles of the near-infrared phosphorescence of singlet oxygen generated by RF have been measured in the absence and presence of l-ascorbic acid (AA, vitamin C), 3-O-Ethyl-L-ascorbic acid (3-EtAA) and Trolox (TX, a water-soluble analogue of vitamin E) in phosphate buffer (pH 6.8). These substances suppress the RF-photosensitized singlet oxygen generation. For example, the quantum yield of singlet oxygen generation is decreased to a third by adding 0.4 mmol dm-3 AA or TX (the concentration of dissolved oxygen in air-saturated water is 0.27 mmol dm-3). AA and TX are more efficient suppressors of RF-photosensitized singlet oxygen generation than 3-EtAA. The bimolecular rate constants for quenching of the excited singlet and triplet states of RF by AA, 3-EtAA and TX have been determined through measurements of fluorescence and transient absorption. These measurements suggest that the observed suppression is due to the quenching of the excited singlet and triplet states of RF by AA, 3-EtAA and TX. The bimolecular rate constants for quenching of singlet oxygen by AA, 3-EtAA and TX were determined to be 1.8 × 108, 0.27 × 108, and 4.4 × 108 mol-1 dm3 s-1, respectively.