Retinyl acetate

Iupac Name：[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] acetate

Molecular Weight：328.496

Modify Date.: 2023-02-20 07:00

Introduction: Retinyl acetate (retinol acetate, vitamin A acetate) is a natural form of vitamin A. It is the acetate ester of retinol. It consists of yellow crystals which are greasy or sticky. It has a mild, characteristic odor. It has potential antineoplastic and chemo-preventive activities. It can be used to fortify food with vitamin A. As vitamin A acetate can induce cell differentiation and inhibit cell proliferation, it is used in skin-conditioning agent. View more+

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1. Names and Identifiers

1.1 Name: Retinyl acetate
1.2 Synonyms: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate (9cis)-O15-Acetylretinol 3,7-DIMETHYL-9-(2,6,6-TRIMETHYLCYCLOHEX-1-EN-1-YL)NONA-2,4,6,8-TETRAEN-1-YL ACETATE acetic acid [3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl] ester all-trans-Vitamin Aacetate Arovit Dry Vitamin A Acetate 325CWS/A MFCD00019413 Myvak Myvax NH25735 NSC 122760 O15-Acetylretinol Retinol acetate Retinol, O15-acetyl- Retinol, O15-acetyl-, (9cis)- Retinol,acetate, all-trans- (8CI) Rovimix A 1000 trans-Retinol acetate VITAMIN A ACETATE

1.3 CAS No.: 127-47-9

1.4 CID: 638034

1.5 EINECS(EC#): 204-844-2

1.6 Molecular Formula: C22H32O2 (isomer)

1.7 Inchi: InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9+,18-14+

1.8 InChkey: QGNJRVVDBSJHIZ-QHLGVNSISA-N

1.9 Canonical Smiles: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCOC(=O)C)C)C

1.10 Isomers Smiles: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/COC(=O)C)/C)/C

2. Properties

2.1 Density: 0.968

2.1 Melting point: 58℃

2.1 Boiling point: 440.5 oC at 760 mmHg

2.1 Refractive index: 1.547-1.555

2.1 Flash Point: 124.8 oC

2.1 Precise Quality: 328.24000

2.1 PSA: 26.30000

2.1 logP: 6.08110

2.1 Solubility: absolute ethanol: 25?mg/mL

2.2 Appearance: crystalline

2.3 Storage: Air Sensitive. Store under Nitrogen. Hygroscopic. Light Sensitive. Keep Cold.

2.4 Chemical Properties: Crystalline

2.5 Color/Form: Yellow powder

2.6 Odor: Amine like

2.7 Water Solubility: soluble

2.8 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 234 companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 234 companies. For more detailed information, please visit ECHA C&L website

Of the 18 notification(s) provided by 233 of 234 companies with hazard statement code(s):

H315 (69.53%): Causes skin irritation [Warning Skin corrosion/irritation]
H360 (62.23%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H361 (36.91%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H413 (68.67%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P264, P273, P280, P281, P302+P352, P308+P313, P321, P332+P313, P362, P405, and P501

3.2 Purification Methods: The acetate is separated from retinol by column chromatography, then crystallised from MeOH. [Kofler and Rubin Vitamins and Hormones (NY) 18 315 1960 for purification methods]. Store it in the dark, under N2 or Ar, at 0o. [Beilstein 6 IV 4135.] Retinyl acetateSupplier

3.3 Usage: vitamin precursor

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: R38;R63

4.1 Safety Statements: S36/37;S45

4.1 Safety Profile: Moderately toxic byingestion. Experimental teratogenic andreproductive effects. Questionablecarcinogen with experimental neoplastigenicdata. Mutation data reported. When heatedto decomposition it emits acrid smoke andirritating fumes. See also VITAMIN A.

4.2 WGK Germany: 2

4.2 RTECS: VH6825000

4.2 Safety: Hazard Codes:?Xn,Xi
Risk Statements: 38-63-36/37/38?
R38:Irritating to skin.?
R63:Possible risk of harm to the unborn child.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 36/37-45-37/39-26?
S36/37:Wear suitable protective clothing and gloves.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S37/39:Wear suitable gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS of Retinyl acetate (CAS NO.127-47-9): VH6825000

4.3 Specification: ?Retinyl acetate (CAS NO.127-47-9), its Synonyms are Acetic acid, retinyl ester ; Vitamin A acetate ; Retinol, acetate, all-trans- ; Vitamin A alcohol acetate ; Vitamin A ester ; Vitamin A1 acetate ; Retinol, acetate, all-trans- (8CI) ; all-trans-Retinylacetate ; all-trans-Vitamin A acetate . It is crystalline.

4.4 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	432mg/kg (432mg/kg)	?	United States Patent Document. Vol. #3878202,
mouse	LD50	oral	4100mg/kg (4100mg/kg)	?	Journal of the American Academy of Dermatology. Vol. 6, Pg. 652, 1982.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 1B

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H360 May damage fertility or the unborn child H413 May cause long lasting harmful effects to aquatic life
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

IR : liquid film

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

127-47-9Total: 2 Synthesis Route

59830-43-2

127-47-9 264 Suppliers

68-26-8 222 Suppliers

Literatures:
US3960967 A1, ;
Yield: null

12190-75-9

59839-81-5

127-47-9 264 Suppliers

68-26-8 222 Suppliers

Literatures:
US3960967 A1, ;
Yield: null

8. Computational chemical data

Molecular Weight: 328.496g/mol
Molecular Formula: C₂₂H₃₂O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 328.240230259
Monoisotopic Mass: 328.240230259
Complexity: 596
Rotatable Bond Count: 7
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 26.3
Heavy Atom Count: 24
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 4
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB4MAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAGgAAAAAADgCggAICCAAABACIAiDSCAAAAAAgAAAICAAAAAgIBAIAIQACEAAAgAAIoAMAgMAPAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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Vitamin A acetate powder