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(Z)-2-penten-1-ol

(Z)-2-penten-1-ol is a naturally occurring flavor and fragrance alcohol with green, cherry, and floral sensory characteristics.
Chemical Structure

General Material Description

(Z)-2-penten-1-ol, also referred to as cis-2-pentenol or Nor leaf alcohol, is an unsaturated primary alcohol with the molecular formula C5H10O. Classified as a flavor and fragrance compound, it appears as a colorless liquid with characteristic green and slightly fruity notes reminiscent of cherry and floral scents. This compound is linked in professional chemical databases such as PubChem and represents a valuable ingredient derived from nature and synthetic processes. It commonly occurs in essential oils and natural food products, contributing to their distinctive aroma and taste profiles. The compound's sensory profile makes it useful in perfuming agents and flavor applications across food and cosmetic formulations.

Occurrence, Applicability & Potential Uses

(Z)-2-penten-1-ol naturally occurs in a broad range of foods and plants including grilled beef, broadbean, guava, kiwi fruit, mango, oats, olive oil, oysters, passion fruit, petitgrain grapefruit oil, potatoes, sardines, tea, jasmine green tea, and cooked turbot. It serves important roles as a flavor and fragrance agent providing green, cherry, floral, and fruity olfactory notes. This compound is incorporated into both flavoring formulations and perfuming agents. According to the Flavor and Extract Manufacturers Association (FEMA) (US), (Z)-2-penten-1-ol is listed under FEMA number 4305 and is generally recognized as safe for use in food products under specified concentration limits. Additionally, the International Fragrance Association (IFRA) (Global) provides guidelines for its safe use in fragrances.

Physico-Chemical Properties Summary

(Z)-2-penten-1-ol is a moderately volatile, colorless liquid with a molecular weight of approximately 86.13 g/mol. Its specific gravity ranges from about 0.849 to 0.856 at 25 °C, indicating it is less dense than water. The compound exhibits a refractive index between 1.433 and 1.439 at 20 °C. It has a vapor pressure of approximately 2.4 mmHg at 25 °C, reflecting moderate volatility. Its estimated octanol-water partition coefficient (log P) is around 1.15, suggesting moderate hydrophobicity. Solubility is noted to be complete or partial in alcohols and less so in water. The flash point is near 48 °C (119 °F), indicating flammability that requires careful handling. These properties influence its behavior in formulations, affecting volatility, dispersibility, and miscibility characteristics relevant to flavor and fragrance product design.

FAQ

What is (Z)-2-penten-1-ol and how is it classified?
(Z)-2-penten-1-ol, also known as cis-2-pentenol, is an unsaturated primary alcohol with a molecular formula of C5H10O. It is classified as a flavor and fragrance compound found naturally in several fruits, plants, and cooked foods. The compound exhibits a green, slightly fruity odor with cherry and floral nuances and is used in food flavoring and perfumery.
Where is (Z)-2-penten-1-ol naturally found and what are its primary applications?
(Z)-2-penten-1-ol occurs naturally in a variety of foods such as grilled beef, guava, kiwi, mango, oats, olive oil, oysters, passion fruit, potatoes, sardine, and green teas. It is commonly used as a flavor and fragrance agent to provide green, floral, and fruity notes in many food products and cosmetic formulations. Its use is guided by regulatory standards to ensure quality and safety.
What safety regulations and guidelines govern the use of (Z)-2-penten-1-ol?
The compound is listed by the Flavor and Extract Manufacturers Association (FEMA) (US) under FEMA number 4305 and is generally recognized as safe (GRAS) when used within specified limits in flavor applications. The International Fragrance Association (IFRA) (Global) provides recommendations for maximum allowable concentrations in fragrance formulations, such as up to 2% in fragrance concentrates. Safety data indicate it is a flammable irritant with precautionary handling advised. Comprehensive assessments and usage guidelines must be followed according to applicable regional regulations.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

(Z)-pent-2-en-1-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:1576-95-0
Pubchem (cid):5364919
Pubchem (sid):134981189
Flavornet:1576-95-0
Publications by PubMed
Changes in olive oil volatile organic compounds induced by water status and light environment in canopies of Olea europaea L. trees.
Detection of flavor compounds in longissimus muscle from four hybrid pig breeds of Sus scrofa, Bamei pig, and Large White.
Electrophysiological and behavioral responses of male fall webworm moths (Hyphantria cunea) to Herbivory-induced mulberry (Morus alba) leaf volatiles.
Kinetics studies of the gas-phase reactions of NO3 radicals with series of 1-alkenes, dienes, cycloalkenes, alkenols, and alkenals.
Protective group-free syntheses of (±)-frontalin, (±)-endo-brevicomin, (±)-exo-brevicomin, and (±)-3,4-dehydro-exo-brevicomin: racemic pheromones with a 6,8-dioxabicyclo[3.2.1]octane ring.
Freshness characterisation of whiting (Merlangius merlangus) using an SPME/GC/MS method and a statistical multivariate approach.
Kinetics and mechanism of the atmospheric reactions of atomic chlorine with 1-penten-3-ol and (Z)-2-penten-1-ol: an experimental and theoretical study.
Fragrance material review on (Z)-2-penten-1-ol.
Changes in virgin olive oil quality during low-temperature fruit storage.
Analysis of volatile compounds as spoilage indicators in fresh king salmon (Oncorhynchus tshawytscha) during storage using SPME-GC-MS.
Changes in volatile and phenolic compounds with malaxation time and temperature during virgin olive oil production.
[Studies on the chemical constituents of the volatiles of Clerodendron bungei].
Variation of major volatile constituents in various green teas from Southeast Asia.
Dynamic headspace gas chromatography/mass spectrometry characterization of volatiles produced in fish oil enriched mayonnaise during storage.
Lipase specificity toward some acetylenic and olefinic alcohols in the esterification of pentanoic and stearic acids.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2905.29.9000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

General Material Information

Preferred name (Z)-2-penten-1-ol
Trivial Name cis-2-Penten-1-ol
Short Description cis-2-pentenol
Formula C5 H10 O
CAS Number 1576-95-0
FEMA Number 4305
ECHA Number 216-415-7
FDA UNII QNC2NB53MJ
Nikkaji Number J127.236E
MDL MFCD00063208
xLogP3-AA 0.90 (est)
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
Synonyms
  • (2Z)- pent-2-en-1-ol
  • (Z)- pent-2-en-1-ol
  • cis- pent-2-ene-1-ol
  • (Z)- pent-2-enol
  • (Z)-2-penten-1-ol
  • cis-2-penten-1-ol
  • 2-penten-1-ol, (2Z)-
  • 2-penten-1-ol, (Z)-
  • (Z)-2-pentenol
  • cis-2-pentenol
  • (Z)-pent-2-en-1-ol
  • 2-Penten-1-ol, (2Z)-
  • 2-Penten-1-ol, (Z)-
  • (2Z)-2-Penten-1-ol
  • cis-2-Penten-1-ol
  • cis-2-Pentenol
  • Nor leaf alcohol
  • (2Z)-Pent-2-en-1-ol

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 86.133903503418
Specific gravity @ 25 °C
Pounds per Gallon 7.065 to 7.123
Refractive Index 1.433 to 1.439 @ 20 °C
Vapor Pressure 2.408 mmHg @ 25 °C
Vapor Density 1
Flash Point TCC Value 48.33 °C TCC
logP (o/w) 1.146 est
Solubility
alcohol Yes
water, 4.572e+004 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Green
green, phenolic, nasturtium, ethereal, medicinal, aldehydic, cherry, narcissus, metallic, fruity
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity < 1 hour(s) at 100.00 %
Luebke, William tgsc, (2017) At 10.00 % in dipropylene glycol. green phenolic nasturtium ethereal medicinal aldehydic cherry narcissus metallic fruity
Flavor Type: Green
ethereal, green, nasturtium, spicy, mustard, horseradish
Luebke, William tgsc, (2017) Ethereal green nasturtium spicy mustard horseradish
Can add sharp, pungent notes to a variety of sweet and savory applications. Slight sharp, mustard, horse radish

Occurrences

Potential Uses

Applications
Odor purposes Cherry , Floral , Fruit , Green
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 10 - Flammable.
R 38 - Irritating to skin.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for (Z)-2-penten-1-ol usage levels up to:
2.0000 % in the fragrance concentrate.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 23
Click here to view publication 23
average usual ppmaverage maximum ppm
baked goods: 10.0000050.00000
beverages(nonalcoholic): 5.0000025.00000
beverages(alcoholic): --
breakfast cereal: 5.0000025.00000
cheese: 7.0000035.00000
chewing gum: --
condiments / relishes: 5.0000025.00000
confectionery froastings: 10.0000050.00000
egg products: --
fats / oils: 5.0000025.00000
fish products: 2.0000010.00000
frozen dairy: 7.0000035.00000
fruit ices: 10.0000050.00000
gelatins / puddings: --
granulated sugar: --
gravies: 20.00000100.00000
hard candy: --
imitation dairy: 7.0000035.00000
instant coffee / tea: --
jams / jellies: 20.00000100.00000
meat products: 2.0000010.00000
milk products: 7.0000035.00000
nut products: --
other grains: 5.0000025.00000
poultry: 2.0000010.00000
processed fruits: 7.0000035.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 5.0000025.00000
snack foods: --
soft candy: --
soups: 5.0000025.00000
sugar substitutes: --
sweet sauces: 5.0000025.00000

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):1576-95-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5364919
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1987
WGK Germany:3
(Z)-pent-2-en-1-ol
Chemidplus:0001576950