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Cinnamyl Alcohol

HCID 5315892
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Grundinformationen

CAS
104-54-1
Standard-SMILES
OC/C=C/c1ccccc1
InChIKey
OOCCDEMITAIZTP-QPJJXVBHSA-N
Summenformel
C9H10O
Durchschnittliche Molmasse
134,17 g/mol
Monoisotopische Masse
134,07316494

Überblick

Cinnamyl alcohol is a primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified). It has a role as a plant metabolite.

Namen und Bezeichner

Bevorzugter Name
Cinnamyl Alcohol
IUPAC
(E)-3-phenylprop-2-en-1-ol
Englischer Name
3-Phenyl-2-propen-1-ol
Summenformel
C9H10O
Molmasse
134.18

Namen und Synonyme

cinnamyl alcohol104-54-1cinnamic alcohol3-PHENYL-2-PROPEN-1-OL(E)-3-phenylprop-2-en-1-ol(E)-cinnamyl alcoholStyryl carbinolStyrone3-Phenylallyl alcoholStyryl alcoholZimtalcohol(E)-3-Phenyl-2-propen-1-ol
Weitere Namen anzeigen
Cinnamyl Alcohol >2-Propen-1-ol, 3-phenyl-, (2E)-C11667500 trans-Cinnamyl-alcohol(E)-3-Phenylprop-2-en-1-ol (Cinnamyl alcohol)
2-Propen-1-ol, 3-phenyl-StyrylcarbinolFEMA No. 2294Alkohol skoricovyNSC-8775SS8YOP444FNSC-623440CHEBI:33227

Datenbank-Bezeichner

CAS
104-54-1、4407-36-7
PubChem CID
5315892
DTXSID
DTXSID301314144
ChEMBL
CHEMBL324794
ChEBI
CHEBI:17177
UNII
SS8YOP444F
EC Number
203-212-3、689-359-8
Nikkaji
J106.769I、J9.304A

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
1,9
Polarare Oberfläche (TPSA)
20,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
2
Schwere Atome
10
Formalladung
0
Komplexität
101

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Other Aromatic Compounds
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics · 3 Einträge

Cosmetics ingredient -> Base; Flavor; Fragrance; Other (Specify)

Cosmetic ingredients (Cinnamyl Alcohol) -> CIR (Cosmetic Ingredient Review)

Masking

SpringerMaterials PropertiesOptical coefficient
Fragrances · 2 Einträge

Fragrance substance (Cinnamic alcohol) -> IFRA amendment 49

Fragrance Ingredient (Cinnamyl alcohol) -> IFRA transparency List

LogP · 2 Einträge

1.700

1.95

Odor · 2 Einträge

ODOR OF HYACINTH

PLEASANT, FLORAL ODOR

TasteBITTER TASTE
Food Additives

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 2033) of reports.

Warning

H302 (15.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2033 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: 2-Propen-1-ol, 3-phenyl-

Hazard Traits - Fragrance Allergen

Regulation (EC) No 1831/2003 (amended)

2-Propen-1-ol, 3-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propen-1-ol, 3-phenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 25-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/12023

Cinnamyl alcohol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2-Propen-1-ol, 3-phenyl-: Human health tier II assessment
Hazards Summary · 1 Eintrag

Cinnamic alcohol was an allergen in 15 of 20 perfume-sensitive patients patch tested. [HSDB] An irritant; [MSDSonline] Positive patch tests reported in perfume industry and food handlers; One of the chemicals in the fragrance mix; [Kanerva, p. 1771] Included in list of established contact allergens in humans; [EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] Danger of skin sensitization; [MAK]

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 3 Einträge

In general, esters containing an aromatic ring system are expected to be hydrolyzed in vivo. Cinnamyl alcohol is hydrolyzed to [DB14184].

ACIDIC & NEUTRAL URINARY METABOLITE OF CINNAMYL ALC WAS IDENTIFIED THROUGH A COMMON METABOLIC SCHEME.

Cinnamyl alcohol is a known human metabolite of beta-methylstyrene.

FDA Pharmacological Classification · 6 Einträge

SS8YOP444F

CINNAMYL ALCOHOL

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

Absorption, Distribution and Excretion · 3 Einträge

Cinnamyl alcohol is 66% absorbed through the skin and shown to be rapidly absorbed from the gut.

Cinnamyl alcohol is metabolized and excreted primarily in the urine and, to a minor extent, in the feces. After oral or intraperitoneal administration to rats and mice, 76–77% of the dose of cinnamyl alcohol was recovered in the urine and feces within 24 h.

CINNAMYL ALC IS EXCRETED UNCHANGED IN NEUTRAL EXTRACT WHEN GIVEN TO RATS.

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 4 Einträge

CIR ingredient: Cinnamyl Alcohol

Used as a fragrance, flavoring agent, deodorant, and chemical intermediate (chemical resistant coatings, photosensitive polymers, and lithographic plates); [HSDB]

AS DEODORANT IN 12.5% SOLN IN GLYCEROL

FRAGRANCE, EG, FOR COLOGNES, SOAPS, AND LOTIONS; FIXATIVE FOR PERFUME BLENDS; IN MFR OF CHEM RESISTANT COATINGS; FLAVORING AGENT FOR FOOD (EG, CANDY, GUM, BEVERAGES); CHEM INTERMEDIATE FOR CINNAMYL ESTERS USED IN PERFUMERY; IN MFG OF PHOTOSENSITIVE POLYMERS & LITHOGRAPHIC PLATES

Zugehörige Reaktionen

13
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 46570
HRID 46570als Produktuspto-grants-1979_11
Reaktionsgleichung von HRID 479263
HRID 479263als Eduktuspto-grants-2003_11
Reaktionsgleichung von HRID 661840
HRID 661840als Eduktuspto-grants-2011_12
Reaktionsgleichung von HRID 843374
HRID 843374als Eduktuspto-grants-2002_04
Reaktionsgleichung von HRID 1355948
HRID 1355948als Eduktuspto-grants-2003_07
Reaktionsgleichung von HRID 1355950
HRID 1355950als Eduktuspto-grants-2003_07
Reaktionsgleichung von HRID 1421359
HRID 1421359als Produktuspto-grants-2000_06
Reaktionsgleichung von HRID 1439169
HRID 1439169als Eduktuspto-grants-1977_11
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FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.0397 @ 35 °C/35 °C
Flavoring AgentsEU Flavoring substances
Color/Form · 3 Einträge

NEEDLES OR CRYSTAL MASS

WHITE TO YELLOWISH SOLID

WHITE NEEDLES FROM PETROLEUM ETHER

Physikochemische Eigenschaften

Schmelzpunkt
34 °C · 34°C
Siedepunkt
250 °C · 250°C(lit.)
Dichte
1.044 · 1.0440
Brechungsindex
1.5819 · 1.5819
storage temp.
Sealed in dry,Room Temperature
Wasserlöslichkeit
Practically insoluble in water
Löslichkeit
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Aggregatzustand
powder to lump to clear liquid
pka
14.61 · 14.61±0.10(Predicted)
Farbe
White or Colorless to Light yellow
Geruch (Odor)
100 % · at 100.00 %. sweet balsam hyacinth spicy green powdery cinnamyl
Geruchsart
balsamic
Merck
14 · 14,2302
InChI
InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+
InChIKey
OOCCDEMITAIZTP-QPJJXVBHSA-N
SMILES
C(O)/C=C/C1=CC=CC=C1
LogP
1.7 · 1.700
FDA Requirements121.1164
Hazard Classes and Categories · 3 Einträge

Acute Tox. 4 (15.5%)

Acute Tox. 4 (100%)

Skin sensitisation - category 1

Toxikologische Informationen

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Human Toxicity ExcerptsPATCH TESTS TO SEVERAL SCREENING SETS OF FRAGRANCE MATERIALS WERE PERFORMED ON 20 PERFUME-SENSITIVE PT. MOST COMMON ALLERGEN WAS CINNAMIC ALC (15 OF 20 PT).

Regulatorische Informationen

FDA Requirements121.1164

Sicherheitsdaten

hs_code
2906.29.6000
RTECS-Nr.
GE2200000
U.S. Exports · 2 Einträge

(1977) No Data

(1979) No Data

U.S. Imports · 2 Einträge

(1977) 6.74X10+5 GRAMS (PRINCPL CUSTMS DISTS)

(1979) 5.00X10+5 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 3 Einträge

2023: <75,000 lb

(1974) 6.81X10+7 G-CONSUMPTION IN FRAGRANCES

(1979) PROBABLY GREATER THAN 9.08X10+5 GRAMS

Industry UsesFixing agent (mordant)
IFRA Fragrance Standards · 6 Einträge

Cinnamic alcohol

Cinnamyl alcohol; 3-Phenylallyl alcohol; 3-Phenyl-2-propen-1-ol; 2-Propen-1-ol, 3-phenyl-; Styrone; Styryl alcohol; Zimtalcohol; Styryl carbinol

IFRA_STD_017.pdf

49

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Restriction: This material should be used only in the limited quantity as stated in the Standard

Methods of Manufacturing · 2 Einträge

MEERWEIN-PONNDORF REDUCTION OF CINNAMALDEHYDE WITH ALUMINUM ISOPROPYLATE OR ETHYLATE; ALKALINE HYDROLYSIS OF STORAX; REDUCTION OF CINNAMAL DIACETATE WITH ACETIC ACID AND IRON FILINGS

OBTAINED ORIGINALLY BY SAPONIFICATION OF CINNAMYL CINNAMATE (STYRACIN). THIS METHOD OF EXTRACTION FROM STORAX IS STILL USABLE. SYNTHETICALLY, BY REDUCTION OF CINNAMALDEHYDE WITH SODIUM OR POTASSIUM HYDROXIDE.

Formulations/PreparationsASSAY: 98% MIN
Household Products · 2 Einträge

Cosmetics product ingredient: Cinnamyl alcohol

Information on 67 consumer products that contain Cinnamyl Alcohol in the following categories is provided:

Use Classification · 6 Einträge

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Cosmetics -> Masking

General Manufacturing Information · 6 Einträge

All Other Chemical Product and Preparation Manufacturing

2-Propen-1-ol, 3-phenyl-: ACTIVE

WHEN SMALL AMT OF IMPURITIES ARE PRESENT AS IN NATURAL ARTICLE (CINNAMYL ALC FROM STORAX), IT REMAINS FLUID AT LOWER TEMPERATURES THAN THE MELTING POINT.

REPORTED USES: NON-ALCOHOLIC BEVERAGES 8.8 PPM; ALCOHOLIC BEVERAGES 5.0 PPM; ICE CREAM, ICES, ETC 8.7 PPM; CANDY 17 PPM; BAKED GOODS 33 PPM; GELATINS & PUDDINGS 22 PPM; CHEWING GUM 720 PPM.

FLAVOR USEFUL IN APRICOT, PEACH, RASPBERRY, PLUM FLAVORS.

OCCURS (IN ESTERIFIED FORM) IN STORAX & IN BALSAM PERU, CINNAMON LEAVES, HYACINTH OIL. OBTAINED BY ALKALINE HYDROLYSIS OF STORAX.

Restriction Limits in the Finished Product (%) · 6 Einträge

0.22 [Products applied to the lips]

0.067 [Products applied to the axillae]

0.25 [Products applied to the face/body using fingertips]

1.2 [Products related to fine fragrances]

0.32 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]

0.25 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]

Anwendungen

Verwenden3-Phenylprop-2-en-1-ol is a reactant in the preparation of isobenzofuranones.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Benzene, [(1E)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propen-1-yl]-Methylcinnamat2H-Pyran, tetrahydro-2-[[(2E)-3-phenyl-2-propen-1-yl]oxy]-ethyl-(E)-cinnamate,ethyl-trans-cinnamate3-Phenyl-2-propyn-1-oltrans-zimtsureCinnamoylchlorid

Nachgelagerte Produkte

FlunarizinCinnamyl chloridetrans-Cinnamaldehyde3-Phenylpropionaldehyd3-Phenylpropan-1-ol