Retinol 视黄醇

CAS 68-26-8 MFCD00001552

化学结构图

68-26-8
SMILES: CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO)C(C)(C)CCC1

化学属性

Mol. FormulaC₂₀H₃₀O
Mol. Weight286.45
Melting PointNo Data Available
Density0.954
Refractive index1.641
Stability对光敏感,对湿度敏感
Boiling Point
Flash Point-26 °C
Appearance crystalline 淡化色片状结晶,熔点62-64℃,沸点120-125℃(0.667Pa)。易溶于油脂或有机溶剂,不溶于水。热稳定性较好,碱性条件下较稳定,酸性条件下不稳定。遇三氯化锑呈特征蓝色反应,易受紫外线和空气中氧的破坏,与维生素C共存时可得到保护。

别名和识别编码

Chemical NameRetinol
Synonym (all-e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen 1 2,4,6,8-Nonatetraen-1-ol, 2,4,6,8-Nonatetraen-1-ol, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-y 21 CFR 182,5930 3,7-DIMETHYL-9-(2,6,6-TRIMETHYL-1-CYCLOHEXENYL)-2,4,6,8-NONATETRAEN-1-OL 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,6,8-tetraen-1-ol 3,7-二甲基-9-(2,6,6-三甲基-1-环己烯基)-2,4,6,8-壬四烯-1-醇 3,7-二甲基-9-(2,6,6-三甲基-1-环已稀) 6-三甲基-1-环己烯-1-基)-2 7-二甲基-9-( AXEROPHTHOL Aoral Aquasol A; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cycl HI-A-Vita RETINOL ALL TRANS ISOMER TRANS VITAMIN A ALCOHOL TRANS-RETINOL all-trans-Retinol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00001552
CAS Number68-26-8
PubChem Substance ID329751561
EC Number200-683-7
Beilstein Registry Number403040
Chemical Name Translation视黄醇
Merck Number13,10073
Wiswesser Line NotationL6UTJ A1 B1U1Y1&U2U1Y1&U2Q C1 C1
LabNetwork Molecule IDLN00194008
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分类

  • {SNA} Carotenoid,
  • {SNA} Carotenoid, Cofactor, Gene Regulation, Isoprenoid, Isoprenoids, Phytochemicals by Chemical Classification, Prenols, Vitamin A, Vitamins, 代谢组学, 代谢通路, 代谢通路图中的代谢产物和辅酶分子, 抗肿瘤药物, 生化试剂, 癌症研究, 细胞生物学, 脂类, 营养研究
  • {SNA} Carotenoid, Isoprenoids, Phytochemicals by Chemical Classification, Prenols, Vitamin A, Vitamins, 生化试剂, 细胞生物学,

产品应用

  • 视黄酸受体(the retinoic acid receptor,RAR) 和类视黄醇受体(the retinoid X receptor,RXR)的配体,作为其转导因子,调控正常和恶性细胞的生长和分化。

相关文献及参考

  • Merck: 14,10013 Beilstein: 6,IV,4130

安全信息

GHS Symbol
WGK Germany3
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H304 May be fatal if swallowed and enters airways 吞食和进入呼吸道可能致命
  • H336 May cause drowsiness or dizziness 肯能导致嗜睡或头晕
  • H411 Toxictoaquaticlifewithlonglastingeffects 对水生生物有毒性并具有长期影响。
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H373 May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官
  • H302 Harmful if swallowed 吞食有害
  • H413 Maycauselonglastingharmfuleffectstoaquaticlife 可能对水生生物造成长期持续有害影响。
  • H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H319 Causes serious eye irritation 严重刺激眼睛
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter dust mask type N95 (US), Eyeshields, Gloves
RTECSVH6750000
Signal word Danger
Precautionary statements
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P301+P310
  • P304+P340+P312
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P331 Do NOT induce vomiting.. 不要催吐。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P305+P351+P338
  • P308+P313
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
Hazard Codes T Xn F,Xn,N Xn,N,F
Risk Statements
  • R38 Irritating to skin 刺激皮肤
  • R22 Harmful if swallowed 吞咽有害
  • R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
  • R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
  • R48/20
  • R11 Highly flammable 非常易燃
  • R62 Possible risk of impaired fertility 有削弱生殖能力的危险
  • R67 Vapours may cause drowsiness and dizziness 蒸汽可能导致嗜睡和昏厥
  • R51/53
  • R65 Harmful: may cause lung damage if swallowed 若吞咽可能伤害肺部器官
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S53 Avoid exposure - obtain special instructions before use 避免接触,使用前获得特别指示说明;
Storage condition - 86 -20°C避光储存。 2-8°C
UN Number UN 1208 3/PG 2
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
REFERENCE :
   CPEDAM Clinical Pediatrics (Philadelphia).  (Lippincott/Harper, Journal
   Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740)  V.1-    1962-
   Volume(issue)/page/year: 21,435,1982

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
REFERENCE :
   AVSUAR Acta Dermato-Venereologica, Supplementum.  (Almqvist & Wiksell, POB
   45150, S-10430 Stockholm, Sweden)  No.1-    1929-  Volume(issue)/page/year:
   74,29,1975

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
REFERENCE :
   51ZKAN "The Retinoids, Vol.2," Sporn, M.B., et al., eds., New York, Academic
   Press, Inc., 1984  Volume(issue)/page/year: 2,287,1984

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
REFERENCE :
   JAADDB Journal of the American Academy of Dermatology.  (C.V. Mosby Co.,
   11830 Westline Industrial Dr., St. Louis, MO 63141)  1979-
   Volume(issue)/page/year: 6,652,1982

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - hamster Cells - not otherwise specified
DOSE/DURATION           : 8 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

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 17 umol/L
REFERE

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 4 mg/L
REFERENCE :
   EJCODS European Journal of Cancer and Clinical Oncology.  (Pergamon Press,
   c/o Elsevier Science, 660 White Plains Rd., Tarrytown, NY 10591)  V.17(7)-
   25, 1981-89.  For publisher information, see EJCAEL Volume(issue)/page/year:
   21,1089,1985

TYPE OF TEST            : DNA inhibition
ROUTE OF EXPOSURE       : Parenteral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 20700 mg/kg/69W (Intermittent)
REFERENCE :
   JJIND8 JNCI, Journal of the National Cancer Institute.  (Washington, DC)
   V.61-79, 1978-87. For publisher information, see J

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 100 umol/L
REFERENCE :
   ONCOBS Oncology.  (S. Karger AG, Postfach CH-4009 Basel, Switzerland) V.21- 
     1967-  Volume(issue)/page/year: 44,356,1987

TYPE OF TEST            : DN

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 4 mg/L
REFERENCE :
   EJCODS European Journal of Cancer and Clinical Oncology.  (Pergamon Press,
   c/o Elsevier Science, 660 White Plains Rd., Tarrytown, NY 10591)  V.17(7)-
   25, 1981-89.  For publisher information, see EJCAEL Volume(issue)/page/year:
   21,1089,1985

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
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
REFERENCE :
   NTOTDY Neurobehavioral Toxicology and Teratology.  (Fayetteville, NY) V.3-8,
   1981-86.  For publisher information, see NETEEC. Volume(issue)/page/year:
   3,1,1981

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 113 mg/kg
SEX/DURATION            : female 10 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   PEDIAU Pediatrics.  (American Academy of Pediatrics, P.O. Box 1034,
   Evanston, IL 60204) V.1-    1948-  Volume(issue)/page/year: 13,556,1954

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE                    : 68 mg/kg
SEX/DURATION            : female 1-39 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - urogenital system
REFERENCE :
   OBGNAS Obstetrics and Gynecology.  (Elsevier Science Pub. Co., Inc., 52
   Vanderbilt Ave., New York, NY 10017)  V.1-    1953- Volume(issue)/page/year:
   43,750,1974

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
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

其他信息

  • 鉴别试验:取试样0.5g,于研钵中研碎,加温水10ml,充分搅拌混合成乳浊状,加10ml乙醇破乳后移入一烧瓶中,再加20ml苯,充分振摇混匀后静置,或经离心分离成两层。取苯层,用20ml水充分振摇洗涤后,分去水层,将苯层在减压下蒸干。将残留物溶于氯仿,配成每ml约含维生素A 10 IU,取其1m1,加5ml三氯化锑试液(TS-33),应呈蓝色,并旋即褪色。
  • 参考质量标准三:GB 14750—93(维生素A) 含量(标示量的) ≥95.0% 酸值(OT一4) ≤2.0 过氧化值(见“01040") ≤1.5ml
  • 所属类别一:食品添加剂: 营养强化剂: 维生素类
  • 所属类别二:饲料添加剂: 维生素添加剂
  • 含量分析:与“维生素A脂肪酸酯油(01041)”相同。
  • 毒性:GRAS(FDA,§182.5930,2000)。 LD 50 2000mg/kg(大鼠,经口)。
  • MOL 文件:68-26-8.mol
  • 用途四:维生素A为一种脂溶性维生素,它以游离醛或酯的开式存在于动物性食物中,在脂肪、蛋白、乳法、肝中含量丰富。植物中不含维生素A,但含维生素A的前身(provitamin A),存在于胡萝卜、番茄等蔬菜中,动动物吸收后,可转化成维生素A。维生素A是维持人体生长、发育、生殖和细胞膜的稳定性所必需的,在视觉过程中起重要作用。视网膜中有感强光的感弱光的两种细胞。感弱光的细胞含有一种色素叫视紫红质,它是在暗环境中由顺视黄醛和视蛋白结合而成的,遇光则分解成反视黄醛和视蛋白,并由此相起神经冲动,传入中枢产生视觉。视黄醛在体内因不断代谢而补消耗,需要及时通过氧化维生素A予以补充。当体仙维生素A缺乏时,视紫红质的合成量随之减少,因而使在弱光中视力减退,这就是夜盲症的原因。维生素A与上能上能下细胞的正常结构和功能有关,,缺乏时会导致辞眼结膜、角膜干燥、发炎,甚至失明,还会造成呼吸道上皮受损,容易发生呼吸道感染、毛发脱落、婴儿发育迟缓等。作为营养增补剂的维生档A油是由水产动物的肝脏、幽门垂所得的脂肪油或其浓缩物。将新鲜鱼类肝脏、幽门垂粉碎,加1-2%氢氧化钠溶液至pH8-9。含油量少的原料,另外添加肝油或鱼油作为稀释用油在搅拌下加热30-60min,使组织消化溶解,析出肝渍,离心分离得到维生素A油。也可采用酶解或溶剂萃取、分子蒸馏使浓缩,使产品中维生素A的浓度达原油的7-8倍。因维生素A油不溶于水,通常添加表面活性剂使其能分散于水中。用于香肠、人造奶油、面包、乳制品、果汁粉、花生白脱等。香肠是最适宜添加维生素A的食品,
  • 溶于无水乙醇、甲醇、氯仿、醚、脂肪和油类,实际上不溶于水或甘油。在农药气中不稳定,极易氧化,紫外线能使其失去效价,其溶液显示特有的蓝色荧光,油溶液则相当稳定。容易氧化成维生素A醛(视黄醛)。
  • 用途一:用于制药片和胶囊,在饲料工业中作为维生素类饲料添加剂
  • F:8-10-16-23
  • 用途五:视黄酸受体(the retinoic acid rec
  • 所属类别三:食品添加剂: 营养强化剂(营养增补剂): 维生素
  • 食品添加剂最大允许使用量最大允许残留量标准:添加剂中文名称 允许使用该种添加剂的食品中文名称 添加剂功能 最大允许使用量(g/kg) 最大允许残留量(g/kg) 维生素A(视黄醇或醋酸视黄酯或棕榈酸视黄醇)[维生素类] 乳及乳饮料 营养强化剂 600~1000μg(1.维生素A添加量均以视黄醇当量计算 2.1μg视黄醇当量=1μg视黄醇=3.33I.U维生素A 3.如用β-胡萝卜素强化可折成维生素A来表示 4.1μgβ-胡萝卜素=0.167μg视黄醇) 维生素A(视黄醇或醋酸视黄酯或棕榈酸视黄醇)[维生素类] 婴幼儿食品、乳制品 营养强化剂 3000~9000μg(1.维生素A添加量均以视黄醇当量计算 2.1μg视黄醇当量=1μg视黄醇=3.33I.U维生素A 3.如用β-胡萝卜素强化可折成维生素A来表示 4.1μgβ-胡萝卜素=0.167μg视黄醇) 维生素A(视黄醇或醋酸视黄酯或棕榈酸视黄醇)[维生素类] 芝麻油、色拉油、人造奶油 营养强化剂 4000~8000μg(1.维生素A添加量均以视黄醇当量计算 2.1μg视黄醇当量=1μg视黄醇=3.33I.U维生素A 3.如用β

系列性分类


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