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68-26-8

68-26-8 structure
68-26-8 structure
  • Name: Vitamin A
  • Chemical Name: all-trans-Retinol
  • CAS Number: 68-26-8
  • Molecular Formula: C20H30O
  • Molecular Weight: 286.452
  • Catalog: API Vitamins and minerals Vitamin AD drugs
  • Create Date: 2018-02-08 08:00:00
  • Modify Date: 2024-01-02 08:28:18
  • Retinol, also known as Vitamin A1, has pleiotropic functions including vison, immunity, hematopoiesis, reproduction, cell differentiation/growth, and development.
Name all-trans-Retinol
Synonyms Alphalin
Lard-factor
Vitamin A1
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol
Vitamin A (USP)
trans-retinol
Vitamine A
Vitaminum A
Retinol
VI-a
Vitamin A
(2E,4E,6E,8E)-3,7-Diméthyl-9-(2,6,6-triméthyl-1-cyclohexén-1-yl)-2,4,6,8-nonatétraén-1-ol
TRANS-VITAMIN A ALCOHOL
all-trans-retinol
(2E,4E,6E,8E)-3,7-diméthyl-9-(2,6,6-triméthylcyclohex-1-én-1-yl)nona-2,4,6,8-tétraén-1-ol
EINECS 200-683-7
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol
Vitamin A1 alcohol, all-trans-
MFCD00001552
Description Retinol, also known as Vitamin A1, has pleiotropic functions including vison, immunity, hematopoiesis, reproduction, cell differentiation/growth, and development.
Related Catalog
Target

Human Endogenous Metabolite

In Vitro It is found that contribution of hepatic microsomes (RDHs) to Retinol metabolism is greater than that of cytosol (ADHs), evidenced by higher Clint (Vmax/Km) of Retinol formation in microsomes than in cytosol[1].
In Vivo The results show that compare with control (CON) rats, high-fat diet (HFD) significantly lowers basal level of Retinol in plasma, but markedly elevates basal levels of Retinol in kidney, adipose tissue and liver. The results show that Retinol absorption in HFD rats is faster than that in CON rats, evidenced by significantly shorter Tmax (3.0±0.0 h for HFD rats vs 5.8±1.1 h for CON rats, p<0.05)[1]. The plasma Retinol levels in methionine-choline deficient diet (MCD) rats are significantly lower than in the controls while the hepatic Retinol levels in MCD rats are markedly higher. The hepatic expression of Retinol-metabolizing enzymes and binding proteins (GRBP-I, ALDH1A1, and ALDH1A2) in MCD rats is significantly higher than that in control rats[2].
Kinase Assay Activity of alcohol dehydrogenases (ADHs)/retinol dehydrogenases (RDHs) and retinal dehydrogenases (RALDHs) are assessed. Briefly, hepatic ADHs/RDHs and RALDHs activities are evaluated with Retinal formation in the presence of β-nicotinamide adenine dinucleotide (β-NAD+) and β-Nicotinamide adenine dinucleotide phosphate (β-NADP+), respectively. The incubation mixture consists of hepatic cytosol/microsomes (at the final concentration of 0.5 mg/mL), and a series concentrations of Retinol, 4.0 mM co-factor, 5 mM MgCl2, 91 μM butylated hydroxytoluene in a total volume of 500 μL. The reaction is initiated by the addition of Retinol pre-incubated for 5 min at 37°C. Following 15 min incubation, the reaction is quenched by extraction with equal volume of n-butanol/methanol, 95:5 (v:v) containing 0.005% butylated hydroxytoluene[1].
Animal Admin Wistar rats (male, aged 4 wk) are used in this study. Two groups of 6 rats are given free access to the following diets: the standard diet (control group) and the methionine-choline deficient diet (MCD) group. Each diet contains Retinol (1000 IU/100g). After 6 wk, the rats are sacrificed by exsanguination under isoflurane anesthesia after an overnight fast. Blood is collected in heparinized tubes, and plasma is separated for storage at -80°C. The liver, intestine, testes, and kidneys are removed, immediately frozen in liquid nitrogen, and stored at -80°C[2].
References

[1]. Zhang M, et al. High-fat diet enhanced retinal dehydrogenase activity, but suppressed retinol dehydrogenase activity in liver of rats. J Pharmacol Sci. 2015 Apr;127(4):430-8.

[2]. Miyazaki H, et al. Retinol status and expression of retinol-related proteins in methionine-choline deficient rats. J Nutr Sci Vitaminol (Tokyo). 2014;60(2):78-85.
Density 1.0±0.1 g/cm3
Boiling Point 421.2±14.0 °C at 760 mmHg
Melting Point 61-63 °C(lit.)
Molecular Formula C20H30O
Molecular Weight 286.452
Flash Point 147.3±16.4 °C
Exact Mass 286.229675
PSA 20.23000
LogP 6.84
Vapour Pressure 0.0±2.3 mmHg at 25°C
Index of Refraction 1.549
Storage condition 2-8°C
Stability Stable, but light and air sensitive. Incompatible with strong acids, strong oxidizing agents.

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VH6750000
CHEMICAL NAME :
Retinol, all trans-
CAS REGISTRY NUMBER :
68-26-8
BEILSTEIN REFERENCE NO. :
0403040
LAST UPDATED :
199706
DATA ITEMS CITED :
60
MOLECULAR FORMULA :
C20-H30-O
MOLECULAR WEIGHT :
286.50
WISWESSER LINE NOTATION :
L6UTJ A1 B1U1Y1&U2U1Y1&U2Q C1 C1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
5475 ku/kg/1Y-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - pleural effusion Gastrointestinal - other changes Musculoskeletal - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1510 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1510 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
73 mL/kg/16D-I
TOXIC EFFECTS :
Musculoskeletal - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
73 mL/kg/16D-I
TOXIC EFFECTS :
Musculoskeletal - other changes Nutritional and Gross Metabolic - changes in calcium Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
68 mg/kg
SEX/DURATION :
female 1-39 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
200 mg/kg
SEX/DURATION :
female 8 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - eye/ear
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
76560 ug/kg
SEX/DURATION :
female 8-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
113 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
150 mg/kg
SEX/DURATION :
female 7-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
683 mg/kg
SEX/DURATION :
female 4-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - other measures of fertility Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
22 mg/kg
SEX/DURATION :
female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
240 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1200 ku/kg
SEX/DURATION :
female 6-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
60060 ug/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
60 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - eye/ear
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
60 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
30 mg/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
150 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
72 mg/kg
SEX/DURATION :
female 11-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
150 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
30 mg/kg
SEX/DURATION :
female 3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - skin and skin appendages
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
120 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
9610 mg/kg
SEX/DURATION :
female 8-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
30 mg/kg
SEX/DURATION :
lactating female 1 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - skin and skin appendages
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
375 mg/kg
SEX/DURATION :
female 7-11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
45045 ug/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - eye/ear
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
145 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
145 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
145 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
180 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - gastrointestinal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
96 mg/kg
SEX/DURATION :
female 11-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
480 mg/kg
SEX/DURATION :
female 11-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
12 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
480 mg/kg
SEX/DURATION :
female 10-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
120 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
240 mg/kg
SEX/DURATION :
female 14-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - hepatobiliary system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
45 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
77 mg/kg
SEX/DURATION :
female 8-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
52550 ug/kg
SEX/DURATION :
female 9-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
DNA inhibition
TYPE OF TEST :
DNA inhibition

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Rodent - hamster Cells - not otherwise specified
DOSE/DURATION :
24 mg/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 246,67,1991 *** REVIEWS *** TOXICOLOGY REVIEW CLPTAT Clinical Pharmacology and Therapeutics (St. Louis). (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1960- Volume(issue)/page/year: 5,480,1964 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW EVHPAZ EHP, Environmental Health Perspectives. (U.S. Government Printing Office, Supt of Documents, Washington, DC 20402) No.1- 1972- Volume(issue)/page/year: 15,121,1976 TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 6,351,1979 TOXICOLOGY REIVEW NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB-275-754 TOXICOLOGY REVIEW JACTDZ Journal of the American College of Toxicology. (Mary Ann Liebert, Inc., 1651 Third Ave., New York, NY 10128) V.1-12, 1982-1993. Discontinued. Volume(issue)/page/year: 6(3),279,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X1676 No. of Facilities: 546 (estimated) No. of Industries: 3 No. of Occupations: 7 No. of Employees: 12809 (estimated) No. of Female Employees: 9075 (estimated)
Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Danger
Hazard Statements H317-H319-H360-H413
Precautionary Statements P201-P280-P305 + P351 + P338-P308 + P313
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn: Harmful;F: Flammable;N: Dangerous for the environment;
Risk Phrases R22;R38
Safety Phrases S36/37-S61-S62
RIDADR UN 1208 3/PG 2
WGK Germany 3
RTECS VH6750000
Hazard Class 3.0
HS Code 3004500000
HS Code 3004500000

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