DL-α-Tocopherol CAS 10191-41-0
Introduction：Basic information about DL-α-Tocopherol CAS 10191-41-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
DL-α-Tocopherol Basic information
| Product Name: | DL-α-Tocopherol |
| Synonyms: | ALL-RAC-ALPHA-TOCOPHEROL;(+/-)-ALPHA-TOCOPHEROL;(+/-)-ALPHA-TOCOFEROL;ALPHA-TOCOPHEROLUM;ALPHA-DL-TOCOPHEROL;5,7,8-TRIMETHYLTOCOL;A-TOCOPHEROL;IRGANOX E 201 |
| CAS: | 10191-41-0 |
| MF: | C29H50O2 |
| MW: | 430.71 |
| EINECS: | 233-466-0 |
| Product Categories: | Other APIs;Antioxidant;Biochemistry;Vitamins;Organics;MX |
| Mol File: | 10191-41-0.mol |
DL-α-Tocopherol Chemical Properties
| Melting point | 2-4°C |
| Boiling point | 200-220°C 0,1mm |
| alpha | [α]D20 - 0.02 - +0.02゜ (neat) |
| density | 0.950 g/mL at 20 °C(lit.) |
| vapor pressure | <1 hPa ( 20 °C) |
| refractive index | n |
| Fp | 240°C |
| storage temp. | 2-8°C |
| solubility | H2O: insoluble |
| pka | 11.40±0.40(Predicted) |
| form | Pale yellow oil |
| color | Colourless to Dark Yellow |
| PH | 7 (20°C, 50g/L in H2O, slurry) |
| Odor | at 100.00?%. bland |
| biological source | synthetic |
| Water Solubility | Miscible with chloroform, vegetable oils, ether, acetone and alcohol. Immiscible with water. |
| Sensitive | Light Sensitive |
| Merck | 14,9495 |
| BRN | 94012 |
| Major Application | food and beverages |
| Cosmetics Ingredients Functions | SKIN CONDITIONING - OCCLUSIVE ANTIOXIDANT FRAGRANCE SKIN CONDITIONING - MISCELLANEOUS |
| InChI | 1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3 |
| InChIKey | GVJHHUAWPYXKBD-IEOSBIPESA-N |
| SMILES | CC(C)CCCC(C)CCCC(C)CCCC1(C)CCc2c(C)c(O)c(C)c(C)c2O1 |
| LogP | 12.2 at 25℃ |
| CAS DataBase Reference | 10191-41-0(CAS DataBase Reference) |
| EPA Substance Registry System | 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)- (10191-41-0) |
Safety Information
| Hazard Codes | Xi,T,F |
| Risk Statements | 36/37/38-39/23/24/25-23/24/25-11 |
| Safety Statements | 26-37/39-45-36/37-16-7 |
| RIDADR | UN1230 - class 3 - PG 2 - Methanol, solution |
| WGK Germany | 1 |
| RTECS | GA8746000 |
| F | 8-10-23 |
| Autoignition Temperature | 280°C |
| TSCA | TSCA listed |
| HS Code | 29362800 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Skin Sens. 1 |
| Hazardous Substances Data | 10191-41-0(Hazardous Substances Data) |
| Chemical Properties | 1mg = 1.1 IU |
| Chemical Properties | Alpha tocopherol is a natural product. The PhEur 6.0 describesalpha-tocopherol as a clear, colorless or yellowish-brown, viscous,oily liquid. |
| Uses | dl-α-Tocopherol is the racemic analog of α-Tocopherol (T526125), the most bioactive of the naturally occurring forms of Vitamin E. Richest sources are green vegetables, grains, and oils, particularly palm, safflower and sunflower oils.dl-α-Tocopherol is an antioxidant that protects cell membrane lipids from oxidative damage. |
| Uses | DL-α-Tocopherol is used as an antioxidant that protects cell membrane lipids from oxidative damage. |
| Uses | These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements. |
| Definition | ChEBI: 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol is a tocopherol. |
| Production Methods | Naturally occurring tocopherols are obtained by the extraction or molecular distillation of steam distillates of vegetable oils; for example, alpha tocopherol occurs in concentrations of 0.1–0.3% in corn, rapeseed, soybean, sunflower, and wheat germ oils.Beta and gamma tocopherol are usually found in natural sources along with alpha tocopherol. Racemic synthetic tocopherols may be prepared by the condensation of the appropriate methylated hydroquinone with racemic isophytol. |
| General Description | TGF-β3 (transforming growth factor-β3) belongs to the TGF β superfamily. The TGFβ3 gene is mapped to human chromosome 14q24.3 |
| Flammability and Explosibility | Non flammable |
| Pharmaceutical Applications | Alpha tocopherol is primarily recognized as a source of vitamin E,and the commercially available materials and specifications reflectthis purpose. While alpha tocopherol also exhibits antioxidantproperties, the beta, delta, and gamma tocopherols are consideredto be more effective as antioxidants. Alpha-tocopherol is a highly lipophilic compound, and is anexcellent solvent for many poorly soluble drugs.Of widespreadregulatory acceptability, tocopherols are of value in oil- or fat-basedpharmaceutical products and are normally used in the concentrationrange 0.001–0.05% v/v. There is frequently an optimumconcentration; thus the autoxidation of linoleic acid and methyllinolenate is reduced at low concentrations of alpha tocopherol, andis accelerated by higher concentrations. Antioxidant effectivenesscan be increased by the addition of oil-soluble synergists such aslecithin and ascorbyl palmitate. Alpha tocopherol may be used as an efficient plasticizer. It hasbeen used in the development of deformable liposomes as topicalformulations. d-Alpha-tocopherol has also been used as a non-ionic surfactantin oral and injectable formulations. |
| Biochem/physiol Actions | TGF-β3 (transforming growth factor-β3) regulates lymphocyte proliferation, apoptosis, hematopoiesis and embryogenesis to maintain immune homeostasis. TGF-β plays an important role in cell growth, differentiation, and survival. TGF-β3 specifically promotes chondrogenic differentiation.TGF-β3 is a strong growth inhibitor for normal and transformed epithelial, lymphoid, fibroblast, and keratinocyte cells. TGF-2 inhibits antitumor action of NK (natural killer) cells, T-cells, macrophages, monocytes and neutrophils. TGF-β3 is a tumor suppressor in the early stages of carcinogenesis, but in the later stages acts as a tumor promoter by inducing epithelial-mesenchymal transition and stimulating angiogenesis. TGF-β isoforms is known to participate in wound healing and tissue fibrosis. TGF-β3 is crucial for tissue restoration and scarless tissue repair. Mutation in the TGFβ3 gene is associated with development of non-syndromic cleft palate only (NS CPO), a rare congenital disease. |
| Safety | Tocopherols (vitamin E) occur in many food substances that areconsumed as part of the normal diet. The daily nutritionalrequirement has not been clearly defined but is estimated to be3.0–20.0 mg. Absorption from the gastrointestinal tract is dependentupon normal pancreatic function and the presence of bile.Tocopherols are widely distributed throughout the body, with someingested tocopherol metabolized in the liver; excretion of metabolitesis via the urine or bile. Individuals with vitamin E deficiency areusually treated by oral administration of tocopherols, althoughintramuscular and intravenous administration may sometimes beused. Tocopherols are well tolerated, although excessive oral intakemay cause headache, fatigue, weakness, digestive disturbance, andnausea. Prolonged and intensive skin contact may lead to erythemaand contact dermatitis. The use of tocopherols as antioxidants in pharmaceuticals andfood products is unlikely to pose any hazard to human health sincethe daily intake from such uses is small compared with the intake ofnaturally occurring tocopherols in the diet. The WHO has set an acceptable daily intake of tocopherol usedas an antioxidant at 0.15–2.0 mg/kg body-weight. |
| storage | Tocopherols are oxidized slowly by atmospheric oxygen andrapidly by ferric and silver salts. Oxidation products includetocopheroxide, tocopherylquinone, and tocopherylhydroquinone,as well as dimers and trimers. Tocopherol esters are more stable tooxidation than the free tocopherols but are in consequence lesseffective antioxidants. Tocopherols should be stored under an inert gas, in an airtightcontainer in a cool, dry place and protected from light. |
| Purification Methods | Dissolve dl--tocopherol in anhydrous MeOH (15mL/g) cool to -6o for 1hour, then chill in a Dry-ice/acetone bath; crystallisation is induced by scratching with a glass rod. The dl--acetate [52225-20-4] (see DL-vitamin E actetate below) is a viscous yellow liquid with m -7o, b 184o/0.01mm, 224o/0.3mm, d 4 20 0.953, n D 20 1.496. It is used as a standard for Vitamin E activity where the unit of activity is attained with 1mg of pure dl--acetate. [Friedrich “Vitamins” Water de Guyter Publ, Berlin 1988, Beilstein 17/4 V 168.] |
| Incompatibilities | Tocopherols are incompatible with peroxides and metal ions,especially iron, copper, and silver. Tocopherols may be absorbedinto plastic. |
| Regulatory Status | GRAS listed. Accepted in Europe as a food additive. Included in theFDA Inactive Ingredients Database (IV injections, powder, lyophilizedpowder for liposomal suspension; oral capsules, tablets, andtopical preparations). Included in the Canadian List of AcceptableNon-medicinal Ingredients. Included in nonparenteral medicineslicensed in the UK. |
| References | [1] Patent: WO2004/46127, 2004, A1. Location in patent: Page 6-7 [2] Patent: WO2004/46127, 2004, A1. Location in patent: Page 6-7 [3] Journal of Catalysis, 2007, vol. 251, # 2, p. 388 - 399 |
DL-α-Tocopherol Preparation Products And Raw materials
| Raw materials | 1,2,4-Trimethylbenzene-->TRIMETHYLQUINONE-->3,7,11,15-TETRAMETHYL-2-HEXADECEN-1-OL-->Isophytol-->Trimethylhydroquinone |
