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HCID 445354Erstellt: 27. Oktober 2026

Vitamin A

Aquasol A · Vitamin A Retinol · Vitamin A (mixture) · ROIDEX · ＶＩＴＡＭＩＮ Ａ 500W · Vitamin A USP/EP/BP · TIANFU CHEM--Vitamin A_ · New anti-aging products

https://huagongshe.com/de/chemical/445354

Molekülstruktur von Vitamin A

Identifikatoren & physikalische Daten

CAS No.11103-57-4
SummenformelC20H30O
Durchschnittliche Molmasse286,5 g/mol
Monoisotopische Masse286,22966558 g/mol
SMILESCC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO)C(C)(C)CCC1
InChIKeyFPIPGXGPPPQFEQ-OVSJKPMPSA-N
PubChem CID445354
ChEMBLCHEMBL986
ChEBICHEBI:17336
EC No.200-683-7
DTXSIDDTXSID3023556
Lokaler NameVitamin A

Chemische & physikalische Eigenschaften

XLogP5,7
Polarare Oberfläche (TPSA)20,2
H-Brücken-Donoren1
H-Brücken-Akzeptoren1
Frei drehbare Bindungen5
Schwere Atome21
Formalladung0
Komplexität496
StoffklassenBiological Agents -> Vitamins and Derivatives
ArzneimittelPharmaceuticals -> Listed in ZINC15
LipideLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]
KosmetikaCosmetic ingredients (Retinol) -> CIR (Cosmetic Ingredient Review)Skin conditioning
SpringerMaterials PropertiesAngular frequency
LogP (Verteilungskoeffizient)log Kow = 5.68
LebensmittelzusatzstoffeNUTRIENT SUPPLEMENT -> FDA Substance added to food
Color/FormSolvated crystals from polar solvents, such as methanol or ethyl formate
LöslichkeitPractically insoluble (NTP, 1992)Practically insoluble in water or glycerolsoluble in absolute alcohol, methanol, chloroform, ether, fats and oilsSol in ethanol and acetone and benzeneAll retinol esters are practically insoluble in water, soluble or partly soluble in anhydrous ethanol and miscible with organic solvents. Vitamin A and its esters are very sensitive to the action of air, oxidising agents, acids, light and heat. Carry out the assay and all tests as rapidly as possible, avoiding exposure to actinic light and air, oxidising agents, oxidation catalysts (e.g. copper , iron), acids and heatuse freshly prepared solutions.
Dietary IngredientsVitamin A
Human DrugsBreast FeedingLactationMilk, HumanVitaminsFDA approved drugs -> Active ingredientVitamins and minerals
Siedepunkt279 to 280 °F at 1e-06 mmHg (NTP, 1992)137-138 °C at 1X10-6 mm Hg
Lagerbedingungen-20°C
Kosmetik-Inhaltsstoffe FunktionenSKIN CONDITIONING - MISCELLANEOUS
InChIInChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
InChIKeyFPIPGXGPPPQFEQ-OVSJKPMPSA-N
SMILESC1(/C=C/C(/C)=C/C=C/C(/C)=C/CO)=C(C)CCCC1(C)C
EPA chemische InformationenVitamin A (11103-57-4)

Sicherheit & Vorschriften

GHS-EinstufungThis chemical does not meet GHS hazard criteria for 0.3% (1 of 311) of reports.DangerH302 (15.8%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P318, P321, P330, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 311 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.This chemical does not meet GHS hazard criteria for 1% (1 of 105) of reports.
Regulatorische InformationenChemical: RetinolChemical: Vitamin AStatus: Active Update: 13-10-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/11075Vitamin A: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.Retinol: Does not have an individual approval but may be used under an appropriate group standard
Weitere SicherheitsinformationenEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
BrandgefahrenFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
GesundheitsgefahrenSYMPTOMS: Symptoms of chronic overdose include fatigue, malaise, lethargy, abdominal discomfort, anorexia and vomiting. Skeletal effects include slow growth, hard tender cortical thickening over the radius and tibia, migratory arthralgia and premature closing of the epiphysis. Central nervous system effects include irritability, headache and increased intracranial pressure as manifested by bulging fontanels, papilledema and exophthalmos. Dermatologic effects include fissures of the lips, drying and cracking of the skin, alopecia, scaling, massive desquamation and increased pigmentation. Systemic effects include hypomenorrhea, hepatosplenomegaly, jaundice, leukopenia and vitamin A plasma level over 1200 units. Other effects include painful nodular periosteal swelling, osteoporosis, itching, skin eruptions, ulcerations, drowsiness, alopecia, liver enlargement, diplopia and papilledema.

Anwendungen & Verwendung

History

The structure of vitamin A and some of the important derivatives are shown in Figure 1. The parent structure is all-trans-retinol [CAS: 68-26-8] and its IUPAC name is (all-E)-3,7-dimethyl-9-(2,6,6- trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol. The numbering system for vitamin A derivatives parallels the system used for the carotenoids. In older literature, vitamin A compounds are named as derivatives of trimethyl cyclohexene and the side chain is named as a substituent. For retinoic acid derivatives, the carboxyl group is denoted as C-1 and the trimethyl cyclohexane ring as a substituent on C-9. The structures of vitamin A and β-carotene were elucidated by Karrer in 1930 and several derivatives of the vitamin were prepared by this group. In 1935, Wald isolated a substance found in the visual pigments of the eye and was able to show that this material was identical with Karrer’s retinaldehyde.

Verwenden

vitamin A can act as a keratinization regulator, helping to improve the skin’s texture, firmness, and smoothness. Vitamin A esters, once in the skin, convert to retinoic acid and provide anti-aging benefits. Vitamin A is believed to be essential for the generation and function of skin cells. Continued vitamin A deficiency shows a degeneration of dermal tissue, and the skin becomes thick and dry. Surface application of vitamin A helps prevent skin dryness and scaliness, keeping the skin healthy, clear, and infection resistant. Its skin regeneration properties appear enhanced when combined with vitamin e. Vitamin A is a major constituent of such oils as cod liver and shark, and many fish and vegetable oils. See also retinol; retinoic acid; retinylpalmitate.

Gefahrenübersicht
Oral administration of high doses in adults causes cirrhosis, hemorrhage, anorexia, jaundice, and dermatitis[RTECS] Contraindicated in pregnancy at doses > FDA RDAMay be toxic if more than 25,000 IU/d consumed for longer that 2-3 weeksToxic effects include liver injury and increased intracranial pressure (blurred vision, headaches, and altered mental status)Serum levels may be useful in diagnosis[Olson, p. 69, 446] An irritantHarmful by ingestionTeratogenic effects observed in experimental animals[Sigma-Aldrich MSDS]
FDA-AnforderungenSubstance added directly to human food affirmed as generally recognized as safe (GRAS).Vitamin A used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.Vitamin A acetate used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice. /Vitamin A Acetate/Vitamin A palmitate used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice. /Vitamin A Palmitate/
Reaktive GruppeAlcohols and Polyols
Special ReportsMATTESHEIM RCAN MED ASSOC J 122 (7): 757 (1980) EXPTL USE: REVIEW WITH 44 REFERENCES ON THE INHIBITION OF CARCINOGENESIS BY RETINOIDS.
Reactivity ProfileVITAMIN A is light sensitive. Also air sensitive and heat sensitive. Reacts with strong oxidizing agents. Also can react with acids (NTP, 1992). Can react exothermically with reducing agents to release hydrogen gas.
Air and Water ReactionsPractically water insoluble.
Hazard Classes and CategoriesAcute Tox. 4 (15.8%)Skin Sens. 1 (99%)
BrandbekämpfungFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Erste HilfeEYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. If symptoms (such as redness or irritation) develop, immediately transport the victim to a hospital.
LagerbedingungenVitamin A is unstable in, and should be protected from, air and light. Vitamin A preparations should be stored at a temperature less than 40 °C, preferably between 15-30 °C. Oral vitamin A preparations should be stored in tight, light-resistant containers and the injection should be protected from light and freezing.
Freisetung ohne BrandSMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
EntsorgungsverfahrenSRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
Personal Protective Equipment (PPE)RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
TreatmentThe treatment of hypervitaminosis A consists of immediate withdrawal of the vitamin along with symptomatic and supportive treatment. (L1712)
WechselwirkungenInsulin antagonizes the /teratogenic/ effects /of vitamin A/.The antithyroid compound methylthiouracil increases teratogenic effect /of vitamin A/.Thyroxine antagonizes the teratogenic action of vitamin A.In rats, the incidence of congenital abnormalities in the head due to hypervitaminosis A was increased greatly by appropriate administration of cortisone to the dams.For more Interactions (Complete) data for VITAMIN A (19 total), please visit the HSDB record page.
Unerwünschte WirkungenOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.Excessive levels of natural or synthetic vitamin A can lead to various adverse effects. Vitamin A toxicity, also known as hypervitaminosis A, is more commonly associated with the misuse of vitamin A supplements than with health intervention programs. Toxic reactions can also result from consuming liver products rich in vitamin A or from the overuse of vitamin A preparations. The amount of vitamin A required to cause toxicity varies among individuals, depending on factors such as age and hepatic function.
ExpositionspfadeOral, readily absorbed from the normal gastrointestinal tract
Milk ConcentrationsVitamin A is distributed into breast milk ... .
ToxizitätsübersichtSafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.orgSigns and Symptoms of OverdoseVision:Vitamin A (all-<i>trans</i> retinol) is converted in the retina to the 11-<i>cis</i>-isomer of retinaldehyde or 11-<i>cis</i>-retinal. 11-<i>cis</i>-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-<i>cis</i>-retinal, while attached to opsin in rhodopsin is isomerized to all-<i>trans</i>-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-<i>trans</i>-retinal is then released from opsin and reduced to all-<i>trans</i>-retinol. All-<i>trans</i>-retinol is isomerized to 11-<i>cis</i>-retinol in the dark, and then oxidized to 11-<i>cis</i>-retinal. 11-<i>cis</i>-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to re-synthesize 11-<i>cis</i> retinal rapidly. <br/>Epithelial differentiation: The role of Vitamin A in epithelial differentiation, as well as in other physiological processes, involves the binding of Vitamin A to two families of nuclear retinoid receptors (retinoic acid receptors, RARsand retinoid-X receptors, RXRs). These receptors function as ligand-activated transcription factors that modulate gene transcription. When there is not enough Vitamin A to bind these receptors, natural cell differentiation and growth are interrupted.
Signs and SymptomsAcute toxicity (single ingestion of 7 500 RE or 25 000 IU per kg or more): Signs and symptoms may be delayed for 8 to 24 hours and include: increased intracranial pressure, headache, irritability, drowsiness, dizziness, lethargy, vomiting, diarrhea, bulging of fontanels in infants, diplopia, papilledema. Peeling of skin around mouth may be observed from 1 to several days after ingestion and may spread to the rest of the body.
Natural Pollution SourcesVITAMIN A ... IS FOUND ONLY IN THE ANIMAL KINGDOM. ... /IT/ OCCURS IN MARINE FISH LIVER OILS AND IN THE LIVER OF MOST LAND VERTEBRATES AS WELL AS IN BUTTER FAT AND EGGS.Occurs preformed only in animalsmetabolized from carotenoids, such as beta-carotene
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ The tolerance to two alternative large dosage strengths of vitamin A preparation was determined in a double blind study involving 2471 children in two municipalities in the Philippines. Each child, aged 1-6 yr, not suffering from active zerophthalmia or from nausea and/or vomiting, headache, diarrhea, and fever, was randomly given 1 ml of a syrupy suspension later identified to contain, 0, 30, or 60 mg vitaminA. Clinical evaluation of subjects was done by physicians 24 hr and 1 wk after dosing. Nausea and/or vomiting and headache were twice as common among children given 60 mg than those given 30 mg. Severe vomiting (1.2%) was confined to those given 60 mg. Almost all experienced their symptoms within 24 hr after dosingsymptoms lasted for no more than 12-24 hr. The incidence of diarrhea and fever for vitamin A recipients was not significantly different from that of those receiving placebo./HUMAN EXPOSURE STUDIES/ Studies of hypervitaminosis A in animals and anecdotal reports of accidental vitamin A poisoning in humans suggest impairment of bone remodeling and increased numbers of fractures. Because of the widespread use of high dose vitamin A supplements which may produce subclinical hypervitaminosis associated with decreased bone mass and increased risk of fracture, the relationship between current vitamin A supplement use, serum retinol levels, radial bone mass and fracture history was studied in a geographically defined population of 246 postmenopausal women, 55-80 years of age. More than 36% of this population used a vitamin A supplement with 8% of these consuming an amount in excess of 2000 retinol equivalents/day. Serum retinol was measured using high pressure liquid chromatography and radial bone mass was measured using single photon absorptiometry. After controlling for age, current estrogen replacement, and current thiazide antihypertensive use, no statistically significant relationship between vitamin A supplement use or serum retinol with radial bone mass or fractures was observed./SIGNS AND SYMPTOMS/ Early signs and symptoms of chronic vitamin A intoxication include irritability, vomiting, loss of appetite, headache, dry and pruritic skin, skin desquamation, and erythematous dermatitis./SIGNS AND SYMPTOMS/ In addition to hepatosplenomegaly, pathological changes /after chronic vitamin A intoxication/ in the liver include hypertrophy of fat-storing cells, fibrosis, sclerosis of central veins, and cirrhosis, with resultant portal hypertension and ascites.For more Human Toxicity Excerpts (Complete) data for VITAMIN A (22 total), please visit the HSDB record page.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)vitamin aDILI PositiveIntramuscularDOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ ... Repeated applications of large amounts of vitamin A in ointment to rabbit eyes ... /resulted in/ Blepharoconjunctivitis, with loss of hair from the lids./LABORATORY ANIMALS: Acute Exposure/ /In hypervitaminotic animals/ lesions occur in the bones and result from accelerated resorption of bone and cartilage and formation of new bone. ... Other manifestations ... are anorexia, cutaneous lesions, temporary thickening of skin, exophthalmos, hypoprothrombinemia, and eventually death./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Weanling cross bred pigs (36 or 48) were caged individually and fed diets containing a supplement of vitamin A (experiment 1) or vitamin D3 (experiment 2) at levels representing 1, 5, 10, 25, 50 and 100 times the NRC (1988) estimated requirements, for 4 wk. Growth rate, feed intake and feed/gain ratio were not influenced significantly. In experiment 1 the plasma retinol concentrations were at 4 weeks, respectively, 31.7, 39.4, 43.2, 42.9, 44.4, and 46.3 ug/dL (P < 0.05). In experiment 2, the plasma 25(OH)D3 concentrations were at 2 weeks, respectively, 22.5, 29.5, 35.7, 46.2, 79.9, 135.3 ng/mL (P < 0.001). Histological examination of lung, stomach, kidney, liver and heart indicated no abnormalities, but focal microscopic lesions consistent with osteochondrosis were found in pigs receiving vitamin A at levels over 10 times the requirement. The incidence of osteochondrosis at 2 weeks was, respectively, 0/8, 0/8, 0/8, 0/8, 0/8, and 1/8, and at 4 weeks was, respectively, 0/8, 0/8, 0/8, 2/8, 2/8 and 2/8./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Feeding of vitamin A deficient diet to male weanling rats for 10 wk caused significant reduction in the hepatic cytochrome p450, cytochrome b5, aminopyrine N-demethylase and arylhydrocarbon hydroxylase activities. Contrary to this, the levels of these Phase I enzymes were found to be significantly elevated in all the 3 portions (proximal, middle and distal) of the intestine in deficient animals as compared to corresponding pair fed controls. Of the Phase II enzymes studied, uridine diphosphate-glucuronyltransferase showed a significant decrease whereas glutathione S-transferase showed a significant increase in vitamin A deficient rat liver and small intestine.For more Non-Human Toxicity Excerpts (Complete) data for VITAMIN A (20 total), please visit the HSDB record page.
TSCA-Inventar-StatusTSCA listed
R-Sätze (R)61
GefahrensymboleT
Sicherheitshinweise (S)53-45