Retinyl palmitate

Modify Date: 2024-01-03 09:43:34

Retinyl palmitate Structure
Retinyl palmitate structure
 Common Name Retinyl palmitate
CAS Number 79-81-2 Molecular Weight 524.860
Density 0.9±0.1 g/cm3 Boiling Point 607.5±24.0 °C at 760 mmHg
Molecular Formula C36H60O2 Melting Point 41678ºC
MSDS Chinese USA Flash Point 79.7±21.2 °C
Symbol GHS02 GHS07
GHS02, GHS07		 Signal Word Danger

 Use of Retinyl palmitate


Retinyl palmitate is an ester of Retinol and is the major form of vitamin A found in the epidermis. Retinyl palmitate has been widely used in pharmaceutical and cosmetic formulations.

 Names

Name all-trans-retinyl palmitate
Synonym More Synonyms

 Retinyl palmitate Biological Activity

Description Retinyl palmitate is an ester of Retinol and is the major form of vitamin A found in the epidermis. Retinyl palmitate has been widely used in pharmaceutical and cosmetic formulations.
Related Catalog
Target

Human Endogenous Metabolite

In Vitro Retinyl palmitate has a high molecular weight and a stable formulation. To be active, Retinyl palmitate should be enzymatically converted in the skin to retinol by cleavage of the ester linkage and must then be converted to tretinoin via oxidative processes[1].
In Vivo The topical administration of Retinyl palmitate in rats results in increased protein and collagen and an epidermal thickening[1].
References

[1]. Oliveira MB, et al. Topical application of retinyl palmitate-loaded nanotechnology-based drug delivery systems for the treatment of skin aging. Biomed Res Int. 2014;2014:632570.

 Chemical & Physical Properties

Density 0.9±0.1 g/cm3
Boiling Point 607.5±24.0 °C at 760 mmHg
Melting Point 41678ºC
Molecular Formula C36H60O2
Molecular Weight 524.860
Flash Point 79.7±21.2 °C
Exact Mass 524.459351
PSA 26.30000
LogP 14.83
Appearance of Characters oil
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.508
Storage condition 2-8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VH6860000
CHEMICAL NAME :
Retinol, all-trans-, palmitate
CAS REGISTRY NUMBER :
79-81-2
BEILSTEIN REFERENCE NO. :
1917366
LAST UPDATED :
199701
DATA ITEMS CITED :
38
MOLECULAR FORMULA :
C36-H60-O2
MOLECULAR WEIGHT :
524.96
WISWESSER LINE NOTATION :
L6UTJ A1 B1U1Y1&U2U1Y1&U2OV15 C1 C1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
7910 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 :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6060 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 :
4760 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5250 ku/kg/21D-I
TOXIC EFFECTS :
Liver - other changes Musculoskeletal - other changes Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
13750 ug/kg
SEX/DURATION :
female 35 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
36 mg/kg
SEX/DURATION :
male 26 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
248 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
16500 ug/kg
SEX/DURATION :
female 8-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
206 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 - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
275 mg/kg
SEX/DURATION :
female 8 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 :
Oral
DOSE :
440 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 :
138 mg/kg
SEX/DURATION :
female 16 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
275 mg/kg
SEX/DURATION :
female 11 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 :
Intraperitoneal
DOSE :
82500 ug/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 :
Intraperitoneal
DOSE :
413 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1350 mg/kg
SEX/DURATION :
female 11-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
275 mg/kg
SEX/DURATION :
female 7 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 - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
275 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
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 :
Subcutaneous
DOSE :
275 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
660 mg/kg
SEX/DURATION :
female 8-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
262 mg/kg
SEX/DURATION :
female 11 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 :
1321 mg/kg
SEX/DURATION :
female 8-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Specific Developmental Abnormalities - gastrointestinal system Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
660 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 - Specific Developmental Abnormalities - skin and skin appendages
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
220 mg/kg
SEX/DURATION :
female 8 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 :
Intraperitoneal
DOSE :
330 mg/kg
SEX/DURATION :
female 8 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 :
Intraperitoneal
DOSE :
28 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 :
Intraperitoneal
DOSE :
220 mg/kg
SEX/DURATION :
female 10 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)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
330 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death 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 :
Intraperitoneal
DOSE :
28 mg/kg
SEX/DURATION :
female 10 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 :
Intraperitoneal
DOSE :
110 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 :
Intraperitoneal
DOSE :
2750 ug/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
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 :
2750 ug/kg
SEX/DURATION :
female 13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Human Fibroblast
DOSE/DURATION :
27500 ug/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 58,317,1978 *** REVIEWS *** 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 : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80573 No. of Facilities: 221 (estimated) No. of Industries: 4 No. of Occupations: 10 No. of Employees: 9773 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80573 No. of Facilities: 893 (estimated) No. of Industries: 8 No. of Occupations: 23 No. of Employees: 18737 (estimated) No. of Female Employees: 8842 (estimated)

 Safety Information

Symbol GHS02 GHS07
GHS02, GHS07
Signal Word Danger
Hazard Statements H225-H319
Precautionary Statements P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235
Personal Protective Equipment Eyeshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter
Hazard Codes Xn:Harmful
Risk Phrases R63
Safety Phrases S53-S23-S36/37/39-S45-S36/37
RIDADR UN1170 - class 3 - PG 2 - Ethanol, solution
WGK Germany 3
RTECS VH6860000
HS Code 2936210000

 Synthetic Route

Methyl palmitate structure

Methyl palmitate

CAS#:112-39-0

Retinyl acetate structure

Retinyl acetate

CAS#:127-47-9

~93%

Retinyl palmitate Structure

Retinyl palmitate

CAS#:79-81-2

Literature: DSM IP ASSETS B.V.; BONRATH, Werner; GAA, Alex; STRITT, Claude Patent: WO2014/23772 A1, 2014 ; Location in patent: Page/Page column 9 ;
Retinyl acetate structure

Retinyl acetate

CAS#:127-47-9

Palmitic acid structure

Palmitic acid

CAS#:57-10-3

~78%

Retinyl palmitate Structure

Retinyl palmitate

CAS#:79-81-2

Vitamin A structure

Vitamin A

CAS#:68-26-8

Literature: Eastman Chemical Company Patent: US7566795 B2, 2009 ; Location in patent: Page/Page column 11 ;
Retinyl acetate structure

Retinyl acetate

CAS#:127-47-9

Palmitic acid structure

Palmitic acid

CAS#:57-10-3

~73%

Retinyl palmitate Structure

Retinyl palmitate

CAS#:79-81-2

Literature: Zhu, Kai; Wang, Jianqiang; Wang, Yan-Hua; Liu, Hui; Han, Ping-Fang; Wei, Ping Journal of Nanoscience and Nanotechnology, 2011 , vol. 11, # 9 p. 7593 - 7602
Pyridine structure

Pyridine

CAS#:110-86-1

Vitamin A structure

Vitamin A

CAS#:68-26-8

Palmitoyl chloride structure

Palmitoyl chloride

CAS#:112-67-4

~%

Retinyl palmitate Structure

Retinyl palmitate

CAS#:79-81-2

Literature: Journal of the American Chemical Society, , vol. 64, p. 2407,2410 Helvetica Chimica Acta, , vol. 32, p. 489,498 Vitamins Hormones, , vol. 18, p. 301
Vitamin A structure

Vitamin A

CAS#:68-26-8

Palmitoyl chloride structure

Palmitoyl chloride

CAS#:112-67-4

~%

Retinyl palmitate Structure

Retinyl palmitate

CAS#:79-81-2

Literature: Journal of the American Pharmaceutical Association, Scientific Edition, , vol. 49, p. 458 - 462

 Customs

HS Code 2936210000

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 Synonyms

Retinol, O-(1-oxohexadecyl)-
EINECS 201-228-5
O-hexadecanoylretinol
Retinyl palmitate
all-trans-retinyl palmitate
O-Palmitoylretinol
Retinol hexadecanoate
VITAMIN A PALMITATE
[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] hexadecanoate
MFCD00019414
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Related Compounds: More...
retinyl palmitate
34356-29-1
dehydroretinyl palmitate
95632-86-3
4,4-Difluororetinyl palmitate
91484-94-5
retinyl 4-phenylbutyrate
880089-30-5
retinyl hexadecyl ether
85563-59-3
Retinyl acetate-d4
118139-40-5
[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] 2,2-dimethylpropanoate
20559-05-1
retinyl bromoacetate
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retinyl cyclohexylacetate
1018814-13-5
Cyclopentanol, 1-[[[4-(aminomethyl)phenyl]thio]methyl]-
1564638-19-2
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2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
134104-43-1
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131615-57-1
(4-Methyl-tetrahydro-furan-2-yl)-methanol
6906-52-1
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
930439-75-1
(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)(2-chlorophenyl)methanone
1823182-32-6
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
1018584-77-4
tert-Butyl-DL-alanine
1375289-11-4
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