(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl hexadecanoate

• ChemBase ID: 73067
• Molecular Formular: C22H38O7
• Molecular Mass: 414.53292
• Monoisotopic Mass: 414.26175356
• SMILES: O1[C@@H](C(=C(C1=O)O)O)[C@H](COC(=O)CCCCCCCCCCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H]([C@H]1OC(=O)C(=C1O)O)O
• InChI: InChI=1S/C22H38O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(24)28-16-17(23)21-19(25)20(26)22(27)29-21/h17,21,23,25-26H,2-16H2,1H3/t17-,21+/m0/s1
• InChIKey: QAQJMLQRFWZOBN-LAUBAEHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl hexadecanoate
• IUPAC Traditional name: ascorbyl palmitate
• Synonyms: Ascorbic palmitate; Ascorbyl monopalmitate; L-Ascorbyl 6-palmitate; 6-O-Palmitoyl-L-ascorbic acid; 6-O-Palmitoyl-L-ascorbic acid; L-Ascorbyl palmitate; Ascorbic acid 6-palmitate; L-Ascorbic acid 6-palmitate; Ascorbyl palmitate; L-Ascorbic acid 6-hexadecanoate; 6-O-Palmitoylascorbic acid; Ascorbyl palmitate; Ascorbic acid 6-palmitate; L-抗坏血酸棕榈酸酯; L-抗坏血酸 6-棕榈酸酯; 抗坏血酸-6-棕榈酸酯; L-抗坏血酸棕榈酸酯; 抗坏血酸棕榈酸酯; 抗坏血酸棕榈酸酯

Database IDs

• CAS Number: 137-66-6
• EC Number: 205-305-4
• MDL Number: MFCD00005377
• Beilstein Number: 96552
• PubChem SID: 24886958; 24857513; 162037987; 24890608
• PubChem CID: 5282506; 54680660
• CHEMBL: 220190
• Chemspider ID: 16736579
• Unique Ingredient Identifier: QN83US2B0N
• Wikipedia Title: Ascorbyl_palmitate

CALCULATED PROPERTIES

• Acid pKa: 4.4510617
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.922825
• LogD (pH = 7.4): 2.1592975
• Log P: 5.007495
• Molar Refractivity: 110.6235 cm^3
• Polarizability: 43.71489 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Very slightly soluble in water; freely soluble in ethanol
• Apperance: Crystalline; White to yellowish colored powder
• Melting Point: 113-114°C; 113-116 °C; 115-118 °C(lit.); 116–117 °C
• Flash Point: 178.1 °C
• Optical Rotation: [α]20/D +22.9°, c = 2 in methanol; [α]20/D +23±1°, c = 1% in ethanol

Safety Information

• Storage Condition: -20°C
• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (RT); 95%; 98%; 99%
• Salt Data: Free Base
• Suitability: meets USP testing specifications
• Ignition Residue: ≤0.2% (as SO4)
• Cation Traces: Ca: ≤50 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤100 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Loss on Drying: ≤0.2% loss on drying
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C22H38O7

DETAILS

Selleck Chemicals - S2532

Research Area: Cancer
Biological Activity:
L-Ascorbyl 6-palmitate is a synthetic lipophilic ascorbic acid derivative. L-Ascorbyl 6-palmitate is an effective preservative in foods and an effective dietary antitumor promoter in mice. Studies indicate that dietary AP is a source of tissue vitamin C in animals. Besides, dietary L-Ascorbyl 6-palmitate possesses weak antiscorbutic activity in guinea pigs and enhances vitamin C nutriture in humans. In a study, daily mean weight loss during repletion in control animals receiving placebo was significantly greater than that for both L-ascorbic acid (AA) and L-Ascorbyl 6-palmitate animals for days 3–10 of repletion. Daily mean weight loss for AP animals was significantly greater than that for AA animals on days 5 and 6 of repletion. By comparing areas of the weight-time curve during repletion, L-Ascorbyl 6-palmitate appeared to be about 50% as effective as AA in reversing scurvy. [1]

Sigma Aldrich - 76183

Packaging
25, 100 g in poly bottle
Biochem/physiol Actions
L-Ascorbyl palmitate (Asc-6P) is used along with other fatty acid ascorbates such as L-ascorbyl oleate and L-ascorbyl linoleate to protect cells and membranes from oxidative damage. Fatty acid ascorbate molecules have increased solubility in non-polar (lipophilic) environments.

REFERENCES

• Jonker D et al. Toxicology. 1988 Nov 30; 52(3)