Retinol

HCID 445354CAS 11103-57-4

기본 정보

표준 SMILES
CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO)C(C)(C)CCC1
InChIKey
FPIPGXGPPPQFEQ-OVSJKPMPSA-N
분자식
C20H30O
평균 분자량
286.5 g/mol
단동위원소 질량
286.22966558

개요

Vitamin a appears as yellow crystals or orange solid. Practically water insoluble. (NTP, 1992)

이름 및 식별자

우선 이름
Retinol
IUPAC
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
영어명
Vitamin A
분자식
C20H30O
분자량
286.46

이름 및 동의어

retinolall-trans-Retinol68-26-8Agoncaltrans-retinolVeroftalBentavit AHomagenets AoralSehkraft ATestavol Sall-trans-Vitamin AAll-trans retinol
이름 더 보기
Aquasol AVitamin A RetinolVitamin A (mixture)ROIDEXVITAMIN A 500WVitamin A USP/EP/BPTIANFU CHEM--Vitamin A_New anti-aging productsWater-soluble vitamin A3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,6,8-tetraen-1-ol
Super AAxerophtholumWachstumsvitaminVitaminum AVitamine ARetinoloRetinolumRetinol, all trans-

데이터베이스 식별자

CAS
11103-57-4、68-26-8
PubChem CID
445354
DTXSID
DTXSID3023556
ChEMBL
CHEMBL986
ChEBI
CHEBI:17336
UNII
G2SH0XKK91
EC Number
200-683-7、234-328-2
Nikkaji
J1.417F

물성

구조 계산 물성

XLogP
5.7
극성 표면적
20.2 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
1
회전 가능 결합 수
5
무거운 원자 수
21

실험 및 물리화학적 성질

Chemical ClassesBiological Agents -> Vitamins and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]
Cosmetics · 2건

Cosmetic ingredients (Retinol) -> CIR (Cosmetic Ingredient Review)

Skin conditioning

SpringerMaterials PropertiesAngular frequency
LogP · 3건

log Kow = 5.68

5.68

5.68

물리화학적 성질

저장 조건
-20 °C · -20°C
용해도
All 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 heat; use freshly prepared solutions.
화장품 원료 기능
피부 컨디셔닝 - 기타
InChI
InChI=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+
InChIKey
FPIPGXGPPPQFEQ-OVSJKPMPSA-N
SMILES
C1(/C=C/C(/C)=C/C=C/C(/C)=C/CO)=C(C)CCCC1(C)C
화학적 성질 · 1건

Retinol acetate: pale-yellow crystals (mp: about 60 °C). Once melted retinol acetate tends to yield a supercooled melt. Retinol propionate: reddish-brown oily liquid. Retinol palmitate: a fat-like, light yellow solid or a yellow oily liquid, if melted (mp: about 26 °C).

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 0.3% (1 of 311) of reports.

Danger

H302 (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.

유해성 정보

Regulatory Information · 5건

Chemical: Retinol

Chemical: Vitamin A

Status: Active Update: 13-10-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/11075

Vitamin 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

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health Hazards · 1건

SYMPTOMS: 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.

Hazards Summary · 1건

Oral administration of high doses in adults causes cirrhosis, hemorrhage, anorexia, jaundice, and dermatitis; [RTECS] Contraindicated in pregnancy at doses > FDA RDA; May be toxic if more than 25,000 IU/d consumed for longer that 2-3 weeks; Toxic 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 irritant; Harmful by ingestion; Teratogenic effects observed in experimental animals; [Sigma-Aldrich MSDS]

FDA Requirements · 4건

Substance 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/

안전 및 보호

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1건

EYES: 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.

Storage Conditions · 1건

Vitamin 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.

Nonfire Spill Response · 1건

SMALL 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.

Disposal Methods · 1건

SRP: 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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Personal Protective Equipment (PPE) · 1건

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)

독성 정보

TreatmentThe treatment of hypervitaminosis A consists of immediate withdrawal of the vitamin along with symptomatic and supportive treatment. (L1712)
Interactions · 5건

Insulin 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.

Adverse Effects · 2건

Occupational 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.

Exposure RoutesOral, readily absorbed from the normal gastrointestinal tract
Milk ConcentrationsVitamin A is distributed into breast milk ... .
Toxicity Summary · 3건

Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

Signs and Symptoms of Overdose

Vision: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, RARs; and 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.

규제 정보

FDA Requirements · 4건

Substance 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/

안전 데이터

tsca
TSCA listed
risk_code
61
hazard_code
T
safety_code
53-45

화학 및 산업

약리 정보

ATC Code · 6건

D - Dermatologicals

A - Alimentary tract and metabolism

R - Respiratory system

S - Sensory organs

QR - Respiratory system

QD - Dermatologicals

Bionecessity · 5건

Vitamin A deficiency leads to xerophthalmia, Bitot's spots, keratomalacia, night blindness (nyctalopia), hyperkeratosis of the skin, epithelial metaplasia of mucous membranes, and decreased resistance to infections. Administration of vitamin A completely reverses signs of vitamin deficiency unless keratomalacia has resulted in irreversible ocular damage.

Changes in the bronchorespiratory epithelium from mucus secretion to keratinization lead to increased incidence of respiratory infections ... there is also a decrease in elasticity of the lung and other tissues.

State of Deficiency: Urinary calculi are frequent concomitants of vitamin A deficiency. ... Abnormalities of reproduction include impairment of spermatogenesis, degeneration of testes, abortion, resorption of fetuses, and production of malformed offspring.

Often both taste and smell are impaired in Vitamin A deficient individual. Hearing may also become impaired. ... Deficiency can interfere with erythropoiesis. ... Nerve lesions, increased cerebrospinal fluid pressure, and hydrocephalus have been reported.

For more Bionecessity (Complete) data for VITAMIN A (9 total), please visit the HSDB record page.

Protein Binding · 1건

Less than 5% of circulating vitamin A is bound to lipoproteins in blood in normal condition, but may be up to 65% when hepatic stores are saturated because of excessive intake. When released from liver, vitamin A is bound to retinol-binding protein (RBP). Most vitamin A circulates in the form of retinol bound to RBP.

Pharmacodynamics · 1건

Vitamin A is effective for the treatment of Vitamin A deficiency. Vitamin A refers to a group of fat-soluble substances that are structurally related to and possess the biological activity of the parent substance of the group called all-<i>trans</i> retinol or retinol. Vitamin A plays vital roles in vision, epithelial differentiation, growth, reproduction, pattern formation during embryogenesis, bone development, hematopoiesis and brain development. It is also important for the maintenance of the proper functioning of the immune system.

Mechanism of Action · 5건

Vision: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. 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, RARs; and 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.

Topical vitamin A can reverse the impairment of wound healing seen in patients receiving corticosteroids, perhaps by restoring the normal inflammatory reaction in the wound. The possibility has been suggested that systemic vitamin A could inhibit the anti-inflammatory effect of systemic corticosteroids.

Retinol arrested proliferation of cultured neuroblastoma cells at concentrations of 50 um. A correlation existed between inhibition of growth and inhibition of ornithine decarboxylase in both neuroblastoma cells and glioma cells with retinol.

In rats exptl-hypervitaminosis A has been shown ... to produce severe damage of the retina, mainly in the pigment epithelium according to electron microscopy. Alcohol dehydrogenase activity was shown to disappear in the pigment epithelium and visual cells ... .

/The authors/ have shown that in an experimental cell culture system consisting of carcinogen-treated 10T1/2 cells, both retinoids and all dietary carotenoids examined can reversibly inhibit neoplastic transformation in the post-initiation phase of carcinogenesis. This activity strongly correlates with their ability to increase gap junctional intercellular communication by up-regulating the expression of the gene CX43 (connexin43). Connexins comprise the structural unit of gap junctions, organelles which allow direct transfer of signals, nutrients and waste products between contacting cells. CX43 is the most widely expressed member of the gap junction family of genes, and we have demonstrated that its expression is strongly down-regulated in human cancers and in several premalignant conditions. When several human tumour cell lines were genetically engineered to conditionally express CX43 under the influence of a tetracycline promoter, their neoplastic phenotype was strongly attenuated. Specifically, induced cells were inhibited from growing in an anchorage-independent manner and, additionally, growth as xenografts in immunocompromised animals was also strongly attenuated. Growth inhibition in suspension was associated both with increased G(1) cell-cycle arrest and with increased apoptosis. /The authors/ propose a model whereby junctional communication allows the transfer of growth inhibitory signals from normal to neoplastic cells and that retinoids and carotenoids, by increasing signal transfer, act to prevent cancer.

Biological Half-Life · 2건

1.9 hours

Hepatic reserves of vitamin A decrease with a half-life of about 50 days in animals ...

용도 및 제조

Uses · 6건

CIR ingredient: Retinol

Essential micronutrient found in animals; [Merck Index] Used as a nutritional supplement for foods; [FDA] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]

Vitamin (antixerophthalmic)

MEDICATION

MEDICATION (VET)

For the treatment of vitamin A deficiency. Vitamin A helps regulate the immune system, which helps prevent or fight off infections by making white blood cells that destroy harmful bacteria and viruses.

U.S. Exports(1972) 1.83X10+8 GRAMS
U.S. Imports · 3건

(1972) 8.12X10+8 GRAMS

(1975) 1.30X10+8 GRAMS

(1984) 9.62X10+8 g /Vitamin A and Provitamin A, Synthetic/

U.S. Production · 3건

(1972) 4.71X10+8 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1985) In the United States, commercial production of synthetic retinol is about 1000 tons /9.08X10+8 g/ per year

Methods of Manufacturing · 2건

... Vitamin A is isolated by liquid-liquid extraction, molecular distillation, and HPLC. Commercial isolation of retinol from natural raw materials starts with fish oils and is conducted in six steps: (1) accumulation of crude vitamin A by the Solexol countercurrent extraction process, (2) short-path distillation of the retinyl esters (200 °C, 400 Pa), (3) ester saponification (KOH, 60 -70 °C, 30 minutes, N2), (4) extraction of retinol with ether, (5) short-path distillation of retinol (120 °C, 400 Pa), and (6) final purification by crystallization from ethyl formate (-35 °C. With the development of efficient processes for the synthesis of vitamin A on a commercial scale, isolation from natural raw materials has lost importance.

REACTION OF BETA-IONONE AND A PROPARGYL HALIDE

Formulations/Preparations · 2건

AQUEOUS SOLN (DISPERSIONS) OF OIL-SOLUBLE VIT ARE PREPARED BY THE USE OF AN EMULSIFYING AGENT SUCH AS POLYSORBATE 80.

There are many types of preparations that contain retinol. These include solutions of pure synthetic retinol and concentrates that contain both retinol and vitamin D in various proportions. Vitamin A capsules contain 3 to 15 mg of retinol (10,000 to 50,000 USP vitamin A units) per capsule: tablets are also available. A water-miscible preparation (15 mg/ml; 50,000 USP units/ml) can be given intramuscularly. Tretinoin (all-trans-retinoic acid; RETIN-A) is available for topical use as a solution (0.05%), a cream (0.05 and 0.1%), and a gel (0.025 and 0.01%). Isotretinoin (13-cis-retinoic acid; ACCUTANE) is available for oral use as 10, 20, and 40 mg capsules.

응용 분야 · 3건

역사The 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.

용도vitamin 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.

일반 설명The provitamin A carotenoids are obtained from plant sources and comprise some of the best sources of this vitamin. The provitamin As are found in deep green, yellow,and orange fruits and vegetables, such as carrots, spinach, broccoli, kale, collard and turnip greens, mangoes, apricots, nectarines, pumpkins, and sweet potatoes. Vitamin A belongs to a class of compounds referred to as the retinoids, which consist of four isoprenoid units joined in a head-to-tail manner. All double bonds in the isoprenoid units are implied to be in the E (trans) configuration unless stated otherwise. Currently, the term retinoid is applied to retinol and its naturally occurring derivatives plus synthetic analogs, which need not have vitamin A activity. Vitamin A is currently used as a generic descriptor for all retinoids that exhibit the biological activity of retinol, the original substance identified as vitamin A. The term vitamin A1 and all-trans retinol have been used to refer to retinol whereas vitamin A2 was used to refer to 3,4-dehydroretinol.

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