2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-
retinal
CAS: 116-31-4
Molecular Formula: C20H28O
2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)- - Names and Identifiers
| Name | retinal |
| Synonyms | retinal E-Retinal Axerophthal trans-Retinal all-E-Retinal alpha-Retinene all-trans-retina All-trans-Retinaldehyde 2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)- 2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)- |
| CAS | 116-31-4 |
| EINECS | 204-135-8 |
| InChI | InChI=1/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8-,17-13+ |
2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)- - Physico-chemical Properties
| Molecular Formula | C20H28O |
| Molar Mass | 284.44 |
| Density | 1.0083 (rough estimate) |
| Melting Point | 61-63°C |
| Boling Point | 366.92°C (rough estimate) |
| Flash Point | 205.4°C |
| Solubility | Soluble in Clear Yellow Solution at 5mg/ml Acetonitrile. |
| Vapor Presure | 2.61E-07mmHg at 25°C |
| Appearance | Yellow to orange powder |
| Color | yellow |
| Storage Condition | -20°C |
| Stability | Hygroscopic, Light Sensitive, Temperature Sensitive |
| Sensitive | Sensitive to light |
| Refractive Index | 1.4500 (estimate) |
| MDL | MFCD00001550 |
| Physical and Chemical Properties | There are 16 stereoisomers. Thirteen have been chemically synthesized, of which the 11-cis isomer is the chromophoric substance in the native opsins. All Type E: crystalline. Melting Point 64-65 °c. 7E,9Z,11E,13E type: Melting point 56-58. |
| Use | An oxidized form of retinol that is a corotenoid component of the visual pigments. |
2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)- - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R38 - Irritating to the skin |
| Safety Description | S22 - Do not breathe dust. S36/37 - Wear suitable protective clothing and gloves. |
| WGK Germany | 3 |
| RTECS | VH6407000 |
| HS Code | 29122990 |
2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)- - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | vitamin a aldehyde, also known as retinol, is the component closest to acid a, which is produced by oxidative fracture of β-carotene. Reduced to obtain retinol, oxidized to obtain retinoic acid. Retinaldehyde is the auxiliary group of rhodopsin. The 11-cis retinol and opsin in the visual cell form a visual pigment. The 11-cis retinol absorbs light and then isomeres into all-trans retinol, which changes the conformation of rhodopsin and initiates nerve impulses to the brain, thereby forming vision. |
| physiological function | retinal is an important signal transduction molecule in eyeball development, which has many different important roles in vertebrate eyeball development. Retinaldehyde In the omentum, this 11-cis-retinal is produced by the enzymatic reaction of all-trans retinal or 11-cis retinol (new vitamin AB). Visual pigments contained in retinal sensory cells. Visual pigment is a kind of visual substance produced by adapting to a specific light environment in the evolution process of natural selection in the animal kingdom. Its chemical essence is actually a pigment protein with chromophore as an auxiliary group. |
| storage conditions | pure retinal solid is sensitive to ultraviolet light and easy to oxidize. it needs to be protected from light and sealed at low temperature. |
| application | retinal is an anti-wrinkle, anti-aging and anti-acne skin care active ingredient. Studies have shown that compared with other commonly used vitamin A derivatives (for example, retinoic acid), retinal is less irritating to the skin and is more suitable for sensitive skin use. In addition, retinoic acid, which is converted into retinoic acid after being metabolized by the human body, also has the effect of treating acne, which can be said to be a multifunctional active additive. Retinaldehyde can be used in various anti-wrinkle, anti-aging and anti-acne skin care product formulas, and the recommended dosage is about 0.05% ~ 0.15%. |
| overview | visual pigments contained in retinal sensory cells. Vitamin A and carotene in food can be converted into retinal in the body through intestinal absorption. Both the rod and cone cells contain retinal, but due to the different structure of the protein it binds to, the response to light stimulation is different. Retinaldehyde exists in the form of 11-cis-retinol in the rod cells at rest. Illumination can transform 11-cis-retinaldehyde into total trans-retinal, causing rhodopsin to decompose and produce vision. In the dark, all-trans retinaldehyde is transformed into 11-cis-retinol under the action of enzymes, and then combines with opsin to form rhodopsin, which is called visual circulation. If vitamin A is deficient and the photochemical reaction of rod cells cannot proceed normally, night blindness will occur. |
| action | retinal is an important signal transduction molecule in eyeball development, which has many different important roles in vertebrate eyeball development. Myopia is a developmental disease. The active expansion of the bulbar and sclera of myopia is an important mechanism of its elongation, and retinal may be a messenger molecule that regulates the elongation of experimental myopia. The relationship between retinal and the occurrence and development of experimental myopia has made certain progress. This study reviews the retinal and its nuclear receptors, the retina and choroid of experimental myopia, progress in the study of retinal alterations in the sclera and the role of retinal as a messenger molecule that transmits signals of ocular elongation from the retina to the sclera. The role of retinoic acid in skin diseases is very extensive, but due to local stimulation, its clinical application is limited to a certain extent. Retinaldehyde is an intermediate metabolite of natural tretinoin, which has similar biological activity to that of tretinoin, and the skin tolerance to it is significantly better than that of tretinoin. This article reviews the metabolism and biological activity of retinal in vivo and skin and its application in dermatology. Although quitting smoking can greatly reduce the risk of lung cancer, in terms of quitting smoking for 20 years, their risk of this cancer is still twice as high as that of never smokers. Research results by American experts show that for such smokers, taking an appropriate amount of retinol (that is, a derivative of vitamin A retinol and retinoic acid) every day can further effectively reduce the possibility of lung cancer. The study was published recently in the Proceedings of the American Cancer Institute. Jonathan M. Kurie, MD, of the M.D. Anderson Cancer Research Center of the University of Texas, in this study, compared the effect of two different retinaldehyde on the retinoic acid beta receptor (RAR beta) in the lung tissue of 226 smokers. The reduction of this receptor is usually considered to be a precursor to the occurrence of precancerous tumors. At the beginning of the experiment, about 60% of volunteers had a decrease in RAR beta receptor number. After taking retinol 9-cisRA for three months (twice a day), it was found that the number of RAR beta receptors in this group of volunteers was significantly increased, but those taking another type of retinol were compared with those in the ineffective control group No significant difference. In addition, experts also believe that such effects of retinal may be different for those who are smoking. |
| Use | β-carotene intermediate. |
| Production method | Vitamin A is catalyzed by alcohol dehydrogenase and coenzymes I and II to form two retinoids, cis and trans. |
Last Update：2024-04-10 22:29:15
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