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Category:pharmaceuticals / chemical synthisis
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Appearance: | yellow to orange crystalline powder (est) |
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Melting Point: | 180.00 to 181.00 °C. @ 760.00 mm Hg
|
| Boiling Point: | 462.80 °C. @ 760.00 mm Hg (est)
|
| Flash Point: | 663.00 °F. TCC ( 350.60 °C. ) (est)
|
| logP (o/w): | 6.300 |
| Shelf Life: | 8.00 month(s) or longer if stored properly. |
| Storage: | refrigerate in tightly sealed containers. |
| air and light sensitive: | store protected from air and light. |
| Soluble in: |
| | alcohol | | | water, 0.1263 mg/L @ 25 °C (est) |
| Insoluble in: |
| | water |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
oral-rat LD50 2000 mg/kg
American Journal of Clinical Nutrition. Vol. 52, Pg. 183, 1990.
intravenous-rat LD50 75 mg/kg
Drugs in Japan Vol. -, Pg. 886, 1995.
intraperitoneal-rat LD50 96 mg/kg
BLOOD: NORMOCYTIC ANEMIA
BEHAVIORAL: ATAXIA
SPINAL CORD: OTHER DEGENERATIVE CHANGES
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.
oral-mouse LD50 1100 mg/kg
American Journal of Clinical Nutrition. Vol. 52, Pg. 183, 1990.
intravenous-mouse LD50 92 mg/kg
United States Patent Document. Vol. #3878202
intraperitoneal-mouse LD50 208 mg/kg
Drugs in Japan Vol. -, Pg. 886, 1995.
|
| Dermal Toxicity: |
subcutaneous-rat LD50 53 mg/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.
subcutaneous-mouse LD50 253 mg/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
BEHAVIORAL: SLEEP
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.
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| Inhalation Toxicity: |
|
Not determined
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Safety in Use Information:
| Category: | | pharmaceuticals / chemical synthisis |
| Recommendation for all-(E)-retinoic acid usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for all-(E)-retinoic acid flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
References:
| | (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 302-79-4 |
| Pubchem (cid): | 444795 |
| Pubchem (sid): | 134973260 |
Other Information:
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEBI: | View |
| CHEMBL: | View |
| Metabolomics Database: | Search |
| KEGG (GenomeNet): | C00777 |
| HMDB (The Human Metabolome Database): | HMDB12874 |
| FooDB: | FDB022710 |
| Export Tariff Code: | 2916.20.0000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
Formulations/Preparations:
•topical: powder (available by nonproprietary name); cream: 0.02% renova emollient (with methylparaben), (orthoneutrogena);0.025% avita (bertek), retin-a (orthoneutrogena); 0.05% renova emollient (with methylparaben) (orthoneutrogena), retin-a (orthoneutrogena), 0.1% retin-a (orthoneutrogena). gel: 0.01% retin-a (with denatured alcohol 90% and butylated hydroxytoluene) (orthoneutrogena, 0.025% avita (bertek), retin-a (with denatured alcohol 90% and butylated bydroxytoluene) (orthoneutrogena). gel (containing nicrospheres): 0.04% retin-a micro (with benzyl alcohol and propylene glycol) (orthoneutrogena), 0.1% retin-a micro with benzyl alcohol and propylene glycol) (orthoneutrogena). solution: 0.05% retin-a (with denatured alcohol 55%, butylated hydroxytoluene, and polyethylene glycol 400) (orthoneutrogena).
•oral: capsules: 10 mg vesanoid (with methylparaben and propylparaben), (roche).
•tretinoin, usp (all-trans-retinoic acid; (retin-a), liquid cream (0.025 to 0.1%), & a gel (0.025% & 0.01%).
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Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| epi- | aberel | | 15-apo-beta- | caroten-15-oic acid | | | dermairol | | (all-E)-3,7- | dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid | | 3,7- | dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2E,4E,6E,8E,-nonatetraenoic acid | | (2E,4E,6E,8E)-3,7- | dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid | | (2E,4E,6E,8E)-3,7- | dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid | | 3,7- | dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-all-trans-tetraenoic acid | | (2E,4E,6E,8E)-3,7- | dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoic acid | | (2E,4E,6E,8E)-3,7- | dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid | | | effederm | | | eudyna | | 2,4,6,8- | nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (2E,4E,6Z,8E)- | | 2,4,6,8- | nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)- | | | retin-a | | all-trans- | retinoic acid | | trans- | retinoic acid | | | tretinoin | | | vesanoid | | all-(E)- | vitamin A acid | | all-trans- | vitamin A acid | | trans- | vitamin A acid | | all-(E)- | vitamin A1 acid | | all-trans- | vitamin A1 acid |
Articles:
| PubMed:Raspberry ketone promotes the differentiation of C3H10T1/2 stem cells into osteoblasts. |
| PubMed:Characterization of suspected illegal skin whitening cosmetics. |
| PubMed:Effects of all-trans retinoic acid, retinol, and β-carotene on murine macrophage activity. |
| PubMed:The effects of retinoic acid on human corneal stromal keratocytes cultured in vitro under serum-free conditions. |
| PubMed:β-Cryptoxanthin uptake in THP-1 macrophages upregulates the CYP27A1 signaling pathway. |
| PubMed:All-transretinoic acid regulates Th1/Th2 balance in CD4+ T cells when GATA-3 is deficient. |
| PubMed:Identification of FDA-approved drugs targeting breast cancer stem cells along with biomarkers of sensitivity. |
| PubMed:A novel application of furazolidone: anti-leukemic activity in acute myeloid leukemia. |
| PubMed:Cytotoxicity and inhibition of intercellular interaction in N2a neurospheroids by perfluorooctanoic acid and perfluorooctanesulfonic acid. |
| PubMed:Vitamin D transport proteins megalin and disabled-2 are expressed in prostate and colon epithelial cells and are induced and activated by all-trans-retinoic acid. |
| PubMed:The role of lipid-activated nuclear receptors in shaping macrophage and dendritic cell function: From physiology to pathology. |
| PubMed:Treatment of preadolescent acne in the United States: an analysis of nationally representative data. |
| PubMed:Embryonic phenotype, β-carotene and retinoid metabolism upon maternal supplementation of β-carotene in a mouse model of severe vitamin A deficiency. |
| PubMed:Development and validation of a fast chromatographic method for screening and quantification of legal and illegal skin whitening agents. |
| PubMed:A screen for disruptors of the retinol (vitamin A) signaling pathway. |
| PubMed:A crucial role for retinoic acid in the development of Notch-dependent murine splenic CD8- CD4- and CD4+ dendritic cells. |
| PubMed:Impact of dietary factors and food processing on food allergy. |
| PubMed:Retinoic acid: a familiar teratogen. |
| PubMed:The formation, occurrence, and function of β-apocarotenoids: β-carotene metabolites that may modulate nuclear receptor signaling. |
| PubMed:Gemfibrozil and fenofibrate, Food and Drug Administration-approved lipid-lowering drugs, up-regulate tripeptidyl-peptidase 1 in brain cells via peroxisome proliferator-activated receptor α: implications for late infantile Batten disease therapy. |
| PubMed:Efficacy of all-trans retinoid acid in preventing nickel induced cardiotoxicity in myocardial cells of rats. |
| PubMed:Oral alitretinoin: a review of the clinical pharmacokinetics and pharmacodynamics. |
| PubMed:Increased exposure of vitamin A by Chrysanthemum morifolium Ramat extract in rat was not via induction of CYP1A1, CYP1A2, and CYP2B1. |
| PubMed:Lycopene induces retinoic acid receptor transcriptional activation in mice. |
| PubMed:Tretinoin cyclodextrin complex (RA/CyD) causes less irritation with an equal antiwrinkle effect compared with conventional tretinoin: clinical and histologic studies of photoaged skin. |
| PubMed:Quantification of retinoid concentrations in human serum and brain tumor tissues. |
| PubMed:Vitamin A deficiency aggravates iron deficiency by upregulating the expression of iron regulatory protein-2. |
| PubMed:Retinoic acid influences neuronal migration from the ganglionic eminence to the cerebral cortex. |
| PubMed:Intestinal CD103+ dendritic cells: master regulators of tolerance? |
| PubMed:Potential interaction of natural dietary bioactive compounds with COX-2. |
| PubMed:Maternal-fetal transfer and metabolism of vitamin A and its precursor β-carotene in the developing tissues. |
| PubMed:All-trans retinoic acid modifies the expression of clock and disease marker genes. |
| PubMed:Acne vulgaris. |
| PubMed:Influence of food on the pharmacokinetics of oral alitretinoin (9-cis retinoic acid). |
| PubMed:[Establishment of embryonic stem cell for evaluation of development neurotoxicity and test the validation of embryonic stem cell]. |
| PubMed:β-Carotene and its cleavage enzyme β-carotene-15,15'-oxygenase (CMOI) affect retinoid metabolism in developing tissues. |
| PubMed:Combination of retinoic acid and ursodeoxycholic acid attenuates liver injury in bile duct-ligated rats and human hepatic cells. |
| PubMed:Sequential treatment with triple combination cream and intense pulsed light is more efficacious than sequential treatment with an inactive (control) cream and intense pulsed light in patients with moderate to severe melasma. |
| PubMed:Annual drug update: 2010 in review. |
| PubMed:[Study on inducing differentiation of mouse embryonic stem cells into neuronal in vitro]. |
| PubMed:Effect of retinoic acid and delta-like 1 homologue (DLK1) on differentiation in neuroblastoma. |
| PubMed:Basic mechanisms of arsenic trioxide (ATO)-induced apoptosis in human leukemia (HL-60) cells. |
| PubMed:Types of hair loss and treatment options, including the novel low-level light therapy and its proposed mechanism. |
| PubMed:All-trans retinoic acid enhances the transport of phase II metabolites of benzo[a]pyrene by inducing the Breast Cancer Resistance Protein expression in Caco-2 cells. |
| PubMed:Vitamin A as a regulator of antigen presenting cells. |
| PubMed:Vitamin A enhances antitumor effect of a green tea polyphenol on melanoma by upregulating the polyphenol sensing molecule 67-kDa laminin receptor. |
| PubMed:Vitamin A upregulates matrix metalloproteinase-9 activity by murine myeloid dendritic cells through a nonclassical transcriptional mechanism. |
| PubMed:Retinoic acid treatment enhances lipid oxidation and inhibits lipid biosynthesis capacities in the liver of mice. |
| PubMed:Vitamin A-not for your eyes only: requirement for heart formation begins early in embryogenesis. |
| PubMed:Wt1 and retinoic acid signaling in the subcoelomic mesenchyme control the development of the pleuropericardial membranes and the sinus horns. |
| PubMed:Comparison of Puerariae Radix and its hydrolysate on stimulation of hyaluronic acid production in NHEK cells. |
| PubMed:Mouse models for unraveling the importance of diet in colon cancer prevention. |
| PubMed:Significance of vitamin A to brain function, behavior and learning. |
| PubMed:All-trans retinoic acid lowers serum retinol-binding protein 4 concentrations and increases insulin sensitivity in diabetic mice. |
| PubMed:Saccharomyces cerevisiae and Candida albicans stimulate cytokine secretion from human neutrophil-like HL-60 cells differentiated with retinoic acid or dimethylsulfoxide. |
| PubMed:[Effect of all-trans retinoic acid deficiency on iron metabolism in rat primary hepatocyte]. |
| PubMed:Vitamin E supplementation does not prevent ethanol-reduced hepatic retinoic acid levels in rats. |
| PubMed:Retinoic acid is a negative physiological regulator of N-cadherin during early avian heart morphogenesis. |
| PubMed:Determination of retinol, retinyl palmitate, and retinoic acid in consumer cosmetic products. |
| PubMed:Loss of anti-proliferative effect of all-trans retinoic acid in advanced stage of breast carcinogenesis. |
| PubMed:Oxidation of endobiotics mediated by xenobiotic-metabolizing forms of human cytochrome. |
| PubMed:Interactions of alpha1-proteinase inhibitor with small ligands of therapeutic potential: binding with retinoic acid. |
| PubMed:The endogenous retinoid metabolite S-4-oxo-9-cis-13,14-dihydro-retinoic acid activates retinoic acid receptor signalling both in vitro and in vivo. |
| PubMed:Immunotherapy in the treatment of food allergy: focus on oral tolerance. |
| PubMed:Natural and adaptive foxp3+ regulatory T cells: more of the same or a division of labor? |
| PubMed:Tolerability of clindamycin/tretinoin gel vs. tretinoin microsphere gel and adapalene gel. |
| PubMed:Successful treatment of moderate to severe melasma with triple-combination cream and glycolic acid peels: a pilot study. |
| PubMed:Retinoic acid decreases adherence of murine myeloid dendritic cells and increases production of matrix metalloproteinase-9. |
| PubMed:Retinoids modulate expression of the endocytic partners megalin, cubilin, and disabled-2 and uptake of vitamin D-binding protein in human mammary cells. |
| PubMed:Dietary retinoic acid affects song maturation and gene expression in the song system of the zebra finch. |
| PubMed:PPAR gamma regulates MITF and beta-catenin expression and promotes a differentiated phenotype in mouse melanoma S91. |
| PubMed:p21 is required for atRA-mediated growth inhibition of MEPM cells, which involves RAR. |
| PubMed:The common environmental pollutant dioxin-induced memory deficits by altering estrogen pathways and a major route of retinol transport involving transthyretin. |
| PubMed:Newer topical therapies for the treatment of acne vulgaris. |
| PubMed:Acne vulgaris. |
| PubMed:Wrinkles. |
| PubMed:[Translocation of p38 MAPK induced by retinoic acid in H9c2 cells]. |
| PubMed:Retinoic acid modulates hepatic iron homeostasis in rats by attenuating the RNA-binding activity of iron regulatory proteins. |
| PubMed:Oral treatment with ACCUTANE does not increase measures of anhedonia or depression in rats. |
| PubMed:Activation of p38/MEF2C pathway by all-trans retinoic acid in cardiac myoblasts. |
| PubMed:All-trans retinoic acid regulates c-jun expression via ERK5 in cardiac myoblasts. |
| PubMed:Neuroprotective effects of natural products: interaction with intracellular kinases, amyloid peptides and a possible role for transthyretin. |
| PubMed:Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate. |
| PubMed:Platelet-derived growth factor C plays a role in the branchial arch malformations induced by retinoic acid. |
| PubMed:Oral Accutane (13-cis-retinoic acid) has no effects on spatial learning and memory in male and female Sprague-Dawley rats. |
| PubMed:Hepatic phosphatidylethanolamine N-methyltransferase expression is increased in diabetic rats. |
| PubMed:Photomutagenicity of anhydroretinol and 5,6-epoxyretinyl palmitate in mouse lymphoma cells. |
| PubMed:PDGF-C controls proliferation and is down-regulated by retinoic acid in mouse embryonic palatal mesenchymal cells. |
| PubMed:Treatment of cutaneous T-cell lymphoma with retinoids. |
| PubMed:PDGF-C participates in branchial arch morphogenesis and is down-regulated by retinoic acid. |
| PubMed:Prevention of retinoic acid-induced early craniofacial abnormalities by folinic acid and expression of endothelin-1/dHAND in the branchial arches in mouse. |
| PubMed:ROS-production-mediated activation of AP-1 but not NFkappaB inhibits glutamate-induced HT4 neuronal cell death. |
| PubMed:A speculative essay on retinoic acid regulation of neural stem cells in the developing and aging olfactory system. |
| PubMed:atRA-induced apoptosis of mouse embryonic palate mesenchymal cells involves activation of MAPK pathway. |
| PubMed:Once and again: retinoic acid signaling in the developing and regenerating olfactory pathway. |
| PubMed:Regulation of dHAND protein expression by all-trans retinoic acid through ET-1/ETAR signaling in H9c2 cells. |
| PubMed:[Establishment and application of fetal rolling palate organ culture model of mouse]. |
| PubMed:Effect of 17beta-oestradiol on transepithelial calcium transport in human intestinal-like Caco-2 cells and its interactions with 1,25-dihydroxycholecalciferol and 9-cis retinoic acid. |
| PubMed:The screening of chemicals for juvenoid-related endocrine activity using the water flea Daphnia magna. |
| PubMed:Chronic oral treatment with 13-cis-retinoic acid (isotretinoin) or all-trans-retinoic acid does not alter depression-like behaviors in rats. |
| PubMed:Polychlorinated biphenyls disturb differentiation of normal human neural progenitor cells: clue for involvement of thyroid hormone receptors. |
| PubMed:All-trans and 9-cis retinoic acids, retinol and beta-carotene chemopreventive activities during the initial phases of hepatocarcinogenesis involve distinct actions on glutathione S-transferase positive preneoplastic lesions remodeling and DNA damage. |
| PubMed:Developmental changes of the expression of the genes regulated by retinoic acid in the small intestine of rats. |
| PubMed:Effects of retinoic acid administration and dietary vitamin A supplementation on leptin expression in mice: lack of correlation with changes of adipose tissue mass and food intake. |
| PubMed:IV-IVC for topically applied preparations--a critical evaluation. |
| PubMed:A high-fat diet generates alterations in nuclear receptor expression: prevention by vitamin A and links with cyclooxygenase-2 and beta-catenin. |
| PubMed:Similarities and differences in the transcriptional regulation of the leptin gene promoter in gastric and adipose cells. |
| PubMed:19-Nor-1,25(OH)2D2 (a novel, noncalcemic vitamin D analogue), combined with arsenic trioxide, has potent antitumor activity against myeloid leukemia. |
| PubMed:An update on the safety and efficacy of topical retinoids. |
| PubMed:All-trans retinoic acid enhances differentiation and influences permeability of intestinal Caco-2 cells under serum-free conditions. |
| PubMed:Dietary retinoic acid induces hindlimb and eye deformities in Xenopus laevis. |
| PubMed:Potentiation of the teratogenic effects induced by coadministration of retinoic acid or phytanic acid/phytol with synthetic retinoid receptor ligands. |
| PubMed:Triiodothyronine treatment attenuates the induction of hepatic glycine N-methyltransferase by retinoic acid and elevates plasma homocysteine concentrations in rats. |
| PubMed:Effect of retinoic acid on leptin, glycerol, and glucose levels in mature rat adipocytes in vitro. |
| PubMed:Evidence for a probable causal relationship between tretinoin, acitretin, and etretinate and intracranial hypertension. |
| PubMed:Modulation of methyl group metabolism by streptozotocin-induced diabetes and all-trans-retinoic acid. |
| PubMed:Prevention of homocysteine thiolactone induced atherogenesis in rats. |
| PubMed:New drugs of 2003. |
| PubMed:Postnatal changes in gene expression of retinal dehydrogenase and retinoid receptors in liver of rats. |
| PubMed:RNA polymerase II association with the phosphoenolpyruvate carboxykinase (PEPCK) promoter is reduced in vitamin A-deficient mice. |
| PubMed:All-trans-retinoic acid rapidly induces glycine N-methyltransferase in a dose-dependent manner and reduces circulating methionine and homocysteine levels in rats. |
| PubMed:Retinoic acid and glucocorticoid treatment induce hepatic glycine N-methyltransferase and lower plasma homocysteine concentrations in rats and rat hepatoma cells. |
| PubMed:Dietary retinoic acid supplementation stimulates intestinal tumour formation and growth in multiple intestinal neoplasia (Min)/+ mice. |
| PubMed:Retinoid receptors and vitamin A deficiency: differential patterns of transcription during early avian development and the rapid induction of RARs by retinoic acid. |
| PubMed:2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) alters the endogenous metabolism of all-trans-retinoic acid in the rat. |
| PubMed:Neural stem cells and cholinergic neurons: regulation by immunolesion and treatment with mitogens, retinoic acid, and nerve growth factor. |
| PubMed:Clinical applications of retinoids in cancer medicine. |
| PubMed:Chromatographic analysis of endogenous retinoids in tissues and serum. |
| PubMed:Effect of retinoic acid on ferritin H expression during brain development and neuronal differentiation. |
| PubMed:Biological variation of retinoids in man. |
| PubMed:Arsenic trioxide as effective therapy for relapsed acute promyelocytic leukemia. |
| PubMed:Regulation of adiponectin and leptin gene expression in white and brown adipose tissues: influence of beta3-adrenergic agonists, retinoic acid, leptin and fasting. |
| PubMed:Recent advances in the treatment of AIDS-related Kaposi's sarcoma. |
| PubMed:Embryonic retinoic acid synthesis is required for forelimb growth and anteroposterior patterning in the mouse. |
| PubMed:Characterization of a new endogenous vitamin A metabolite. |
| PubMed:Resveratrol, a natural product derived from grapes, is a new inducer of differentiation in human myeloid leukemias. |
| PubMed:Evaluation of the developmental toxicity of crocetin on Xenopus. |
| PubMed:Activation and induction of glycine N-methyltransferase by retinoids are tissue- and gender-specific. |
| PubMed:Vitamin A-related compounds, all-trans retinal and retinoic acids, selectively inhibit activities of mammalian replicative DNA polymerases. |
| PubMed:Vitamin A and its derivatives induce hepatic glycine N-methyltransferase and hypomethylation of DNA in rats. |
| PubMed:Porcine intestinal metabolism of excess vitamin a differs following vitamin a supplementation and liver consumption. |
| PubMed:Effect of all-trans retinoic acid on growth of xenograft tumor and its metastasis in nude mice. |
| PubMed:Characterization of nuclear factors that bind to the human thymidylate synthase gene in HL-60 cells differentiated by all-trans retinoic acid treatment. |
| PubMed:Vitamin A and all-trans and 9-cis retinoic acids inhibit cell proliferation during the progression phase of hepatocarcinogenesis in Wistar rats. |
| PubMed:Retinoic acid metabolites in plasma are higher after intake of liver paste compared with a vitamin A supplement in women. |
| PubMed:Phytanic acid and docosahexaenoic acid increase the metabolism of all-trans-retinoic acid and CYP26 gene expression in intestinal cells. |
| PubMed:Teratogenicity of isotretinoin revisited: species variation and the role of all-trans-retinoic acid. |
| PubMed:[Study of the role of cyclin-dependent kinases (CDKs) in retinoic acid (RA) inducing HL-60 cell differentiation]. |
| PubMed:Tretinoin cream 0.02% for the treatment of photodamaged facial skin: a review of 2 double-blind clinical studies. |
| PubMed:Carnosic acid and promotion of monocytic differentiation of HL60-G cells initiated by other agents. |
| PubMed:Retinoid compounds activate and induce hepatic glycine N-methyltransferase in rats. |
| PubMed:Kaposi's sarcoma: new topical treatment approved. |
| PubMed:FDA news. Food and Drug Administration. |
| PubMed:Oral treatment for KS. |
| PubMed:Formation of cleavage products by autoxidation of lycopene. |
| PubMed:Function of vitamin A in vertebrate embryonic development. |
| PubMed:Retinoic acid enhances the rate of olfactory recovery after olfactory nerve transection. |
| PubMed:Use of arginine to reduce the severity of retinoid-induced hypertriglyceridemia. |
| PubMed:Cardiotoxicity of chemotherapeutic agents: incidence, treatment and prevention. |
| PubMed:New treatments and therapeutic strategies for acne. |
| PubMed:Retinoic acid repressed the expression of c-fos and c-jun and induced apoptosis in regenerating rat liver after partial hepatectomy. |
| PubMed:Gel approved for KS. |
| PubMed:The relationship of p53 and stress proteins in response to bleomycin and retinoic acid in the p53 heterozygous mouse. |
| PubMed:Regulation of cellular retinol-binding protein type II gene expression by arachidonic acid analogue and 9-cis retinoic acid in caco-2 cells. |
| PubMed:Leukemia: A model for drug development. |
| PubMed:Low and high responders to pharmacological doses of beta-carotene: proportion in the population, mechanisms involved and consequences on beta-carotene metabolism. |
| PubMed:A hairless mouse model for assessing the chronic toxicity of topically applied chemicals. |
| PubMed:Manganese enhances phosphorylation of a 47 kD protein in retinoic acid-induced HL-60 cells. |
| PubMed:Abnormal ventricular looping and abnormal laterality of the atrial chambers are the main morphogenetic mechanisms of cardiac lesions in cultured rat embryos treated with retinoic acid. |
| PubMed:Control of Drosophila retinoid and fatty acid binding glycoprotein expression by retinoids and retinoic acid: northern, western and immunocytochemical analyses. |
| PubMed:Dietary fatty acids are possible key determinants of cellular retinol-binding protein II gene expression. |
| PubMed:Oral retinoids in the treatment of seborrhoea and acne. |
| PubMed:Peroxisome proliferator enhances gene expression of cellular retinol-binding protein, type II in Caco-2 cells. |
| PubMed:FIRE (fatty acid synthase insulin-responsive element) and ICE (inverted CCAAT element) regulate fatty acid synthase. |
| PubMed:Cloning of chick cellular retinol-binding protein, type II and comparison to that of some mammals: expression of the gene at different developmental stages, and possible involvement of RXRs and PPAR. |
| PubMed:Retinoic acid reverses ethanol-induced cardiovascular abnormalities in quail embryos. |
| PubMed:Vitamin A regulates genes involved in hepatic gluconeogenesis in mice: phosphoenolpyruvate carboxykinase, fructose-1,6-bisphosphatase and 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase. |
| PubMed:Binding of retinoids to beta-lactoglobulin isolated by bioselective adsorption. |
| PubMed:Regulation of the fatty acid synthase gene by retinoic acid in HepG2 cells is mediated by an E-box-containing multihormonal response element and two neighbouring upstream sequences. |
| PubMed:A developmental toxicity study of tretinoin administered topically and orally to pregnant Wistar rats. |
| PubMed:Regulation of ceruloplasmin by retinoic acid in the developing rat. |
| PubMed:Control of Drosophila opsin gene expression by carotenoids and retinoic acid: northern and western analyses. |
| PubMed:Analysis of catalytic action of transglutaminase induced in human promyelocytic leukemia (HL-60) and human hepatoblastoma (HepG2) cells. |
| PubMed:Pharmacokinetics of retinoids in women after meal consumption or vitamin A supplementation. |
| PubMed:The effect of aging and dietary restriction on the retinoylation of nuclear matrix proteins in rats. |
| PubMed:Retinoid (vitamin A) metabolism. |
| PubMed:Regulation of the fatty acid synthase promoter by retinoic acid. |
| PubMed:Update on the diagnosis of and therapy for acute promyelocytic leukemia and chronic myelogenous leukemia. |
| PubMed:[Genetic diagnosis of colorectal cancer]. |
| PubMed:Pharmacokinetics of all-trans-retinoic acid in Japanese patients with acute promyelocytic leukemia. |
| PubMed:Endogenous retinoids in the early avian embryo. |
| PubMed:Application of the modified relative dose response test to pregnant Indonesian women for assessing vitamin A status. |
| PubMed:Melasma. Etiologic and therapeutic considerations. |
| PubMed:Comparative study of Msx-1 expression in early normal and vitamin A-deficient avian embryos. |
| PubMed:Anti-retinoic acid monoclonal antibody localizes all-trans-retinoic acid in target cells and blocks normal development in early quail embryo. |
| PubMed:A preliminary assessment of the toxic and mutagenic potential of steroidal alkaloids in transgenic mice. |
| PubMed:Enhancement of the teratogenicity of all-trans-retinoic acid by maternal restraint stress in mice as a function of treatment timing. |
| PubMed:Maternal restraint stress-enhanced teratogenicity of all-trans-retinoic acid in CD-1 mice. |
| PubMed:Suppression of oncogene-induced transformation by quercetin and retinoic acid in rat liver epithelial cells. |
| PubMed:Manganese stimulates the oxidative burst of differentiated HL-60 cells. |
| PubMed:Retinoic acid up-regulates erythropoietin production in hepatoma cells and in vitamin A-depleted rats. |
| PubMed:Simultaneous determination of 13-cis- and all-trans-retinoic acids and retinol in human serum by high-performance liquid chromatography. |
| PubMed:Probing the retinol-binding site of bovine beta-lactoglobulin. |
| PubMed:The teratogenic metabolites of vitamin A in women following supplements and liver. |
| PubMed:The prevention of adipose differentiation of 3T3-L1 cells caused by retinoic acid is elicited through retinoic acid receptor alpha. |
| PubMed:Induction of normal cardiovascular development in the vitamin A-deprived quail embryo by natural retinoids. |
| PubMed:Glucuronidation of all-trans-retinoic acid in liposomal membranes. |
| PubMed:Retinoic acid receptor gamma 2 gene expression is up-regulated by retinoic acid in 3T3-L1 preadipocytes. |
| PubMed:Retinoic acid-induced HL-60 cell differentiation is augmented by copper supplementation. |
| PubMed:Comparison of the therapeutic effects of a new arotinoid, Ro 40-8757, and all-trans- and 13-cis-retinoic acids on rat breast cancer. |
| PubMed:Copper is required to maintain Cu/Zn-superoxide dismutase activity during HL-60 cell differentiation. |
| PubMed:[Clinical application of vitamin A, D and E against malignant tumor in human]. |
| PubMed:Embryotoxicity study of propenoic acid, 3-(4-methoxyphenyl)-3-methylbutylester in the Wistar rat. |
| PubMed:The next generation: new chemotherapy agents for the 1990s. |
| PubMed:Lipoprotein lipase enzyme expression in 3T3-L1 adipocytes is posttranscriptionally down-regulated by retinoic acid. |
| PubMed:The nurse consultant's role in products liability litigation. |
| PubMed:FDA scrutinizes 'off-label' promotions. |
| PubMed:Production of a hybridoma cell line secreting retinoic acid-specific monoclonal antibody. |
| PubMed:Effect of retinoic acid and apo-RBP on serum retinol concentration in acute renal failure. |
| PubMed:Synthesis and biochemical characteristics of nucleoproteins following a toxic dose of retinoic acid in cycling and differentiating HL-60 cells. |
| PubMed:Synthesis and phosphorylation of nuclear matrix proteins following a toxic dose of retinoic acid in cycling and differentiating HL-60 cells. |
| PubMed:Induction of malformations in the cynomolgus monkey with 13-cis retinoic acid. |
| PubMed:Effect of butylated hydroxytoluene on bilineage differentiation of the human HL-60 myeloblastic leukemia cell. |
| PubMed:Effect of retinol and retinoic acid supplemented diets on cytochrome P-450 content and UDP glucuronosyltransferase activities in vitamin A-deficient rat liver. |
| PubMed:Effect of tetrachlorodibenzo-p-dioxin (TCDD) on the glucuronidation of retinoic acid in the rat. |
| PubMed:Proto-oncogene expression during retinoic acid-induced neural differentiation of embryonal carcinoma cells. |
| PubMed:Osteotoxicity after chronic dietary administration of 13-cis-retinoic acid, retinyl palmitate or selenium in mice exposed to tumor initiation and promotion. |
| PubMed:Overview of recent clinical pharmacokinetic studies with acitretin (Ro 10-1670, etretin). |
| PubMed:Oxidation of retinol to retinoic acid as a requirement for biological activity in mouse epidermis. |
| PubMed:Food increases the bioavailability of acitretin. |
| PubMed:Increased retinoic acid metabolism following 3,3',4,4',5,5'-hexabromobiphenyl injection. |
| PubMed:Inhibition of 7,12-dimethylbenz[a]anthracene-induced genotoxicity in Chinese hamster ovary cells by retinol and retinoic acid. |
| PubMed:FDA ponders approaches to curbing adverse effects of drug used against cystic acne. |
| PubMed:Reiterations: birth defects caused by isotretinoin and smoking and tobacco use as addicting. |
| PubMed:Birth defects caused by isotretinoin--New Jersey. |
| PubMed:Acne drug controversy ignites turf battle over prescribing. |
| PubMed:Anti-acne drug poses dilemma for FDA. |
| PubMed:Leads from the MMWR. Birth defects caused by isotretinoin--New Jersey. |
| PubMed:Birth defects caused by isotretinoin--New Jersey. |
| PubMed:Induction of ceruloplasmin synthesis by retinoic acid in rats: influence of dietary copper and vitamin A status. |
| PubMed:Vitamin A in human nutrition. |
| PubMed:Modulation of ultraviolet light-, ethyl methanesulfonate-, and 7,12-dimethylbenz[a]anthracene-induced unscheduled DNA synthesis by retinol and retinoic acid in the primary rat hepatocyte. |
| PubMed:[How do I treat acne and rosacea?]. |
| PubMed:Revisions in isotretinoin labeling. |
| PubMed:[Studies on therapeutic effect of 13-cis retinoic acid and squalene on symptoms of PCDFs poisoning in monkeys]. |
| PubMed:Principal components analysis of haematological data from F344 rats with bladder cancer fed N-(ethyl)-all-trans-retinamide. |
| PubMed:Isotretinoin and pregnancy. |
| PubMed:Effects of retinoic acid on rat bone. |
| PubMed:Effects of a large dose of retinol or retinoic acid on the thyroid hormones in the rat. |
| PubMed:Vitamin A and carotene in animal nutrition. |
| PubMed:Food increases the bioavailability of isotretinoin. |
| PubMed:Effect of N-(4-hydroxyphenyl) retinamide on food intake, growth, and mammary gland development in rats. |
| PubMed:Interactions of ultraviolet radiation, 12-O-tetradecanoyl-phorbol-13-acetate and retinoic acid in the skin of hairless mice. |
| PubMed:Isotretinoin in severe, recalcitrant cystic acne: a review. |
| PubMed:Isotretinoin: a word of caution. |
| PubMed:Blood level studies of all-trans- and 13-cis-retinoic acids in rats using different formulations. |
| PubMed:The effects of retinoic acid on the growth of mandible and long bone in fetal rats. |
| PubMed:Sex differences in the effects of retinoids on carcinogenesis by N-nitrosobis(2-oxopropyl)amine in Syrian hamsters. |
| PubMed:Biochemical controls of liver cholesterol biosynthesis. |
| PubMed:Retinoids in experimental diets. |
| PubMed:Growth, appetite, sequence of pathological signs and survival following the induction of rapid, synchronous vitamin A deficiency in the rat. |
| PubMed:Newer treatment in dermatology. |
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an important regulator of gene expression during growth and development, and in neoplasms. tretinoin, also known as retinoic acid and derived from maternal vitamin a, is essential for normal growth; and embryonic development. an excess of tretinoin can be teratogenic. it is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. it has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute). Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912). It is an important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute). [HMDB]
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3D/inchi