3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate

• ChemBase ID: 102843
• Molecular Formular: C22H32O2
• Molecular Mass: 328.48828
• Monoisotopic Mass: 328.24023026
• SMILES: CC(=O)OC/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C
• Canonical SMILES: CC(=O)OC/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C
• InChI: InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3
• InChIKey: QGNJRVVDBSJHIZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate
• IUPAC Traditional name: 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate; vitamin A acetate
• Synonyms: Vitamin A acetate in gelatin, 500,000 I.U./g; (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-4,6,8-nonatetraen-1-ol Acetate; Vitamin A1 Acetate; all-trans-Retinol Acetate; Retinyl acetate; Retinol acetate; VITAMIN A ACETATE; Vitamin A₁ acetate; Acetylretinol; all-trans-Retinol acetate; all-trans-Retinyl acetate; all-trans-Vitamin A acetate;; Retinyl acetate; Vitamin A (acetate); Retinyl acetate; Vitamin A acetate; trans-Retinol Acetate; trans-RETINYL ACETATE; 乙酸维生素A, 在凝胶中, 粉末, 500,000 I.U./g; 维生素 A 醋酸酯; 视黄醇乙酸酯; 醋酸维生素 A; 维生素 A 乙酸酯; 视黄醇乙酸酯

Database IDs

• CAS Number: 127-47-9
• EC Number: 204-844-2
• MDL Number: MFCD00019413
• Beilstein Number: 1915439
• Merck Index: 1410013
• PubChem SID: 24899359; 24899401; 162090091; 24890098; 24899372; 24890097; 24870469
• PubChem CID: 638034
• Chemspider ID: 553599
• Wikipedia Title: Retinyl_acetate

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.1352186
• LogD (pH = 7.4): 5.1352186
• Log P: 5.1352186
• Molar Refractivity: 107.0749 cm^3
• Polarizability: 40.131332 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: absolute ethanol: soluble25 mg/mL (lit.); Chloroform; Dichloromethane; Ether; Ethyl Acetate
• Apperance: crystalline solid or supercooled liquid; matrix dispersion; Pale Yellow Solid; solid or viscous liquid
• Melting Point: ~58 °C(lit.); 57 - 58°C; 57-58 °C; 57-58°C

Safety Information

• Storage Condition: 0°C, Store Under Nitrogen; -20°C Freezer; 2-8°C
• Storage Warning: Light & Air Sensitive & Hygroscopic
• RTECS: VH6825000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 2; 3
• Risk Statements: 63; 63-38; R38-R63
• Safety Statements: 36/37; S36/37
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• NFPA704:
  

  1

  1

  0
• GHS Hazard statements: H315-H361; H361
• GHS Precautionary statements: P281; P281-P201-P202-P308+P313-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: ~95% all-trans-isomer basis
• Grade: analytical standard
• Salt Data: Free Base
• Potency: ~2,800,000 I.U. per g; 2,600,000-2,940,000 I.U. per g
• Packaging: ampule of 100 mg
• Suitability: meets USP testing specifications; suitable for cell culture
• Impurities: ~5% 13-cis-isomer
• Contains: DL-α-tocopherol as stabilizer
• Biological Source: synthetic
• Quality: concentrate (~50% (w/w) in peanut oil)
• Feature: standard type fat soluble vitamin
• Empirical Formula (Hill Notation): C22H32O2

DETAILS

MP Biomedicals - 02103257

Dry: 500,000 IU/g

MP Biomedicals - 02190652

Crystalline

Sigma Aldrich - 95140

Caution
crystallized product can be liquidified by heating to 65°C
Other Notes
isomeric purity: ~95% all-trans- and ~5% 13-cis-isomer
Review: Systematic mode of action of vitamin A1
Unit Definition
1 U corresponds to 1 international unit acc. to Ph Eur II, 217 (1983)
Physical form
may partially crystallize
Biochem/physiol Actions
Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain.Retinoids also exist as retinyl esters such as retinyl propionate, retinyl acetate and retinyl palmitate. Retinyl esters provide pools of vitamin A that are converted into retinol and other retinoids as needed. Retinyl acetate is used in a wide range of biological applications.

Sigma Aldrich - R4632

Analysis Note
Activity based on HPLC comparison to USP standard.
Physical form
Packaged as a melt and may exist as a crystalline solid or a supercooled viscous liquid
Biochem/physiol Actions
Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain.Retinoids also exist as retinyl esters such as retinyl propionate, retinyl acetate and retinyl palmitate. Retinyl esters provide pools of vitamin A that are converted into retinol and other retinoids as needed. Retinyl acetate is used in a wide range of biological applications.

Sigma Aldrich - R7882

Other Notes
All trans
Preparation Note
The melting point of this material is approx. 58 °C. In order to package, it was melted and may exist as a crystalline solid or as a supercooled viscous liquid.
General description
Retinyl-acetate (aka Vitamin A) is found in classical media formulations such as M-199; NCTC-109 and William’s Medium E. Vitamin A is a component of serum use to supplement classical media, consequently most serum containing cell culture systems receive some level of vitamin A. The oxidized form of retinol is retinoic acid, which has hormone-like growth factor and differentiation activity for epithelial and related cell types, especially neural cells. Retinoic acid induces embryonic stem cells to differentiate towards neural cells.

Sigma Aldrich - R3250

Analysis Note
Activity based on HPLC comparison to USP standard.
Physical form
Dispersion in cornstarch-gelatin matrix. Oil dispersible
Biochem/physiol Actions
Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain.Retinoids also exist as retinyl esters such as retinyl propionate, retinyl acetate and retinyl palmitate. Retinyl esters provide pools of vitamin A that are converted into retinol and other retinoids as needed. Retinyl acetate is used in a wide range of biological applications.

Sigma Aldrich - 95139

Unit Definition
1 U corresponds to 1 international U acc. to Ph Eur II, 217 (1983)
Physical form
cristalline solid or supercooled viscous liquid

Sigma Aldrich - V7763

Physical form
分布于含蔗糖、食物淀粉、尼泊金甲酯、尼泊金丙酯和山梨酸钾防腐剂的明胶基质中。

Toronto Research Chemicals - V676000

Essential micronutrient.

REFERENCES

• Heilbron, M., et al.: Biochem. J., 26, 1194 (1932)
• Kamm, J.J., et al.: J. Am Acad. Dermatol., 6, 652 (1932)
• Gerster, H., et al.: Int. J. Vitamin. Nutr. Res., 67, 71 (1932)
• Harrison, E.H., et al.: Annu. Rev. Nutr., 18, 259 (1932)