Retinoic acid
Tretinoin
CAS: 302-79-4
Molecular Formula: C20H28O2
Retinoic acid - Names and Identifiers
| Name | Tretinoin |
| Synonyms | TRETINOIN Tretinoin Tretinion retinoic acid VITAMIN A ACID Vitamin A acid Retionoic Acid 15-oxidoretinal TRANS-RETINOIC ACID (9cis)-retinoic acid TRANS VITAMIN A ACID all-trans-Retinoic acid TRETINOIN VITAMIN A ACID VITAMIN A ACID, ALL-TRANS Tretinoin (Retionoic Acid) 2,4,6,8-Nonatetraenoic acid N,N'-hexane-1,6-diyldiacetamide (11cis,13cis)-7,8-dihydroretinoic acid 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid |
| CAS | 302-79-4 |
| EINECS | 206-129-0 |
| InChI | InChI=1/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/p-1/b9-6+,12-11+,15-8+,16-14+ |
| InChIKey | SHGAZHPCJJPHSC-ZVCIMWCZSA-N |
Retinoic acid - Physico-chemical Properties
| Molecular Formula | C20H28O2 |
| Molar Mass | 300.44 |
| Density | 1.0597 (rough estimate) |
| Melting Point | 180-181 °C (lit.) |
| Boling Point | 381.66°C (rough estimate) |
| Flash Point | 350.6°C |
| Water Solubility | insoluble |
| Solubility | DMSO : ≥ 50 mg/mL (166.42 mM);H2O : < 0.1 mg/mL (insoluble) |
| Vapor Presure | 7.55E-10mmHg at 25°C |
| Appearance | Light yellow to yellow (Solid) |
| Color | yellow |
| Merck | 14,8165 |
| BRN | 2057223 |
| pKa | 4.73±0.33(Predicted) |
| Storage Condition | -20°C |
| Stability | Store Dry in Freezer at -20°C for up to 1 year; in Solution at -20°C for up to 3 Months. |
| Sensitive | Light Sensitive |
| Refractive Index | 1.4800 (estimate) |
| MDL | MFCD00001551 |
| Physical and Chemical Properties | Melting point 179-184°C water-soluble insoluble |
| Use | For abnormal acne, ichthyosis and psoriasis vulgaris |
Retinoic acid - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R63 - Possible risk of harm to the unborn child R38 - Irritating to the skin R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S24/25 - Avoid contact with skin and eyes. |
| UN IDs | 3249 |
| WGK Germany | 3 |
| RTECS | VH6475000 |
| FLUKA BRAND F CODES | 7-8-16-23 |
| TSCA | Yes |
| HS Code | 29362100 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 (10 day) in mice, rats (mg/kg): 790, 790 i.p.; 2200, 2000 orally (Kamm) |
Retinoic acid - Reference
| Reference Show more | 1. Li Xingyong, Wei Xiaohui, Li Xixiang, Liu Xiao Shuan, Chen Erlin, Yang Xutao, Wu Guotai. Therapeutic effect of flax lignans on osteoporosis induced by compound factors in rats [J]. Journal of Practical Chinese Medicine, 2016, 32(10):948-950. 2. Li Xinyong, Wei Xiaohui, Li Xixiang, etc. Effects of flax lignans on bone biomechanics and AKP activity in experimental osteoporosis rats [J]. Western Chinese Medicine, 2015, 28(010):37-39. 3. Hou, Tao, et al. "Degraded duck egg white peptide promote calcium uptake and modulate bone formation in the retinoic acid-induced bone loss rat and Caco-2 cell model." Nutrients 9.5 (2017): 490.https://doi.org/10.3390/nu9050490 4. Hou, Tao, et al. "Collagen peptides from crucian skin improve calcium bioavailability and structural characterization by HPLC-ESI-MS/MS." Journal of agricultural and food chemistry 65.40 (2017): 8847-8854.https://doi.org/10.1021/acs.jafc.7b03059 5. [IF=5.717] Tao Hou et al."Desalted Duck Egg White Peptides Promote Calcium Uptake and Modulate Bone Formation in the Retinoic Acid-Induced Bone Loss Rat and Caco-2 Cell Model."Nutrients. 2017 May;9(5):490 6. [IF=5.279] Tao Hou et al."Collagen Peptides from Crucian Skin Improve Calcium Bioavailability and Structural Characterization by HPLC-ESI-MS/MS."J Agr Food Chem. 2017;65(40):8847-8854 7. [IF=5.396] Xue Feng et al."Extraction and characterization of matrix protein from pacific oyster (Crassostrea gigs) shell and its anti-osteoporosis properties in vitro and in vivo."Food Funct. 2021 Oct;12(19):9066-9076 |
Retinoic acid - Introduction
This product is a cell-induced differentiation drug. Tretinoin is a metabolic intermediate of vitamin A, which mainly affects bone growth and epithelial metabolism. By regulating the mitosis of epidermal cells and the renewal of epidermal cells, it promotes normal keratinization, affects epithelial metabolism, and has a significant promotion effect on the growth of epithelial horn cells and the shedding of the stratum corneum, which can promote the removal of existing acne. At the same time, it inhibits new acne; it can prevent the blockage of the keratin bolt and has an inhibitory effect on the synthesis of keratin.
Last Update：2022-10-16 17:24:24
Retinoic acid - Biological activity
Tretinoin prevents the cytotoxicity of H2O2 in cultured human mesangial cells by increasing catalase activity and reduced glutathione content, which varies with dose and time. Tretinoin-incubated mesangial cells result in increased levels of catalase mRNA and gamma-glutamyl-cysteine synthetase (catalytic subunit) mRNA, which is the rate-limiting step in the de novo synthesis of reduced glutathione. Tretinoin up-regulates matrix metalloproteinase-13 and matrix metalloproteinase-8 in human keloid-derived fibroblasts.
Last Update：2023-08-16 21:32:38
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