What is the preferred IUPAC name for Prenol?

The preferred IUPAC name for Prenol is 3-Methylbut-2-en-1-ol. IUPAC nomenclature provides a systematic way to name chemical compounds, ensuring clarity and consistency in scientific communication.

What are some other common names used for Prenol?

Besides its preferred IUPAC name, Prenol is also commonly known as 3,3-Dimethylallyl alcohol. These alternative names are often used in literature or industry.

What is the CAS Registry Number assigned to Prenol?

The CAS Registry Number for Prenol is 556-82-1. This unique numerical identifier, assigned by the Chemical Abstracts Service, helps in precisely identifying the chemical substance across databases and literature.

Where can one find an interactive 3D model of Prenol?

An interactive 3D model of Prenol is available through JSmol, accessible via a link provided in the source material. This allows users to visualize the molecule's spatial arrangement.

What is the ChEBI identifier for Prenol?

The ChEBI (Chemical Entities of Biological Interest) identifier for Prenol is CHEBI:16019. This identifier is used in biological and chemical databases to reference the compound.

What is Prenol's identifier on ChemSpider?

Prenol is identified by the number 10700 on ChemSpider, a chemical database that provides access to information about chemical structures and properties.

What is the ECHA InfoCard number for Prenol?

The ECHA (European Chemicals Agency) InfoCard number for Prenol is 100.008.312. This card provides regulatory information about the substance within the European Union.

What is Prenol's EC Number?

Prenol has an EC Number of 209-141-4. The EC Number is a unique identifier assigned by the European Commission to chemical substances.

What is the PubChem Compound ID (CID) for Prenol?

The PubChem Compound ID for Prenol is 11173. PubChem is a database of chemical molecules and their activities, and this CID allows for specific retrieval of Prenol's data.

What is the UNII for Prenol?

The UNII (Unique Ingredient Identifier) for Prenol is 55MY0HM445. This identifier is used by the FDA and other regulatory bodies to uniquely identify substances.

What identifier does the CompTox Chemicals Dashboard assign to Prenol?

The CompTox Chemicals Dashboard, maintained by the EPA, assigns the identifier DTXSID2027206 to Prenol. This dashboard provides a comprehensive resource for chemical toxicity data.

What is the InChI representation of Prenol?

The standard InChI (International Chemical Identifier) for Prenol is InChI=1S/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3, with the corresponding key being ASUAYTHWZCLXAN-UHFFFAOYSA-N. InChI is a standard way to represent chemical structures in a text string format.

What is the SMILES string for Prenol?

The SMILES (Simplified Molecular Input Line Entry System) string for Prenol is OC\C=C(/C)C. SMILES provides a concise way to represent chemical structures using ASCII characters.

What is the chemical formula for Prenol?

The chemical formula for Prenol is C5H10O. This formula indicates that each molecule of Prenol contains 5 carbon atoms, 10 hydrogen atoms, and 1 oxygen atom.

What is the molar mass of Prenol?

The molar mass of Prenol is 86.132 g/mol. Molar mass is the mass of one mole of a substance, a fundamental property in chemistry for calculations.

What is the density of Prenol?

Prenol has a density of 0.848 g/cm³. Density is a measure of mass per unit volume, indicating how tightly packed the substance is.

What is the melting point of Prenol?

The melting point of Prenol is calculated to be -59 °C (-74 °F; 214 K). This is the temperature at which Prenol transitions from a solid to a liquid state under standard pressure.

What is the boiling point of Prenol?

The boiling point of Prenol is approximately 142 °C (288 °F; 415 K). This is the temperature at which Prenol turns into a vapor under standard pressure.

How soluble is Prenol in water?

Prenol has a solubility of 17 grams per 100 milliliters in water at 20 °C. This indicates it is reasonably soluble in water, meaning a significant amount can dissolve.

What is the partition coefficient (log P) for Prenol?

Prenol has a log P value of 0.91. The partition coefficient measures a chemical's solubility in a lipid-like (octanol) versus water-like (water) environment, providing insight into its behavior in biological systems.

What is the vapor pressure of Prenol at 25 °C?

The vapor pressure of Prenol at 25 °C is extrapolated to be 3.17 hPa. Vapor pressure indicates the tendency of a substance to evaporate or turn into a gas.

What GHS pictograms are associated with Prenol?

Prenol is associated with two GHS pictograms: a flame, indicating it is a flammable liquid, and an exclamation mark, indicating it is harmful if swallowed (acute toxicity category 4). These pictograms are standardized symbols used for hazard communication.

What is the GHS signal word for Prenol?

The GHS signal word for Prenol is 'Warning'. This word is used to indicate a less severe level of hazard compared to 'Danger'.

What are the GHS hazard statements for Prenol?

The GHS hazard statements for Prenol are H226, which means 'Flammable liquid and vapor,' and H302, meaning 'Harmful if swallowed.' These statements provide specific details about the risks associated with the chemical.

What are some key GHS precautionary statements for handling Prenol?

Key GHS precautionary statements for Prenol include keeping it away from heat and ignition sources (P210), keeping the container tightly closed (P233), washing thoroughly after handling (P264), and not eating, drinking, or smoking when using it (P270). These provide guidance on safe handling and storage.

What is the flash point of Prenol?

The flash point of Prenol is 43.3 °C (109.9 °F; 316.4 K). The flash point is the lowest temperature at which a liquid can form an ignitable mixture in air near the surface of the liquid.

What is Prenol, and where does it occur naturally?

Prenol, also known as 3-methyl-2-buten-1-ol, is a natural alcohol and one of the simplest terpenoids. It is found naturally in various fruits and plants, including citrus fruits, cranberry, bilberry, grapes, raspberry, blackberry, tomato, hop oil, coffee, arctic bramble, cloudberry, and passion fruit.

Describe the physical appearance and odor of Prenol.

Prenol is described as a clear, colorless oil. It possesses a fruity odor, which makes it suitable for occasional use in perfumery.

Which companies are known to manufacture Prenol industrially?

Prenol is manufactured industrially by companies such as BASF in Ludwigshafen, Germany, and Kuraray in Asia. These companies produce it as an intermediate for pharmaceuticals and aroma compounds.

What was the estimated global production volume of Prenol in 2001?

In 2001, the global production of Prenol was estimated to be between 6,000 and 13,000 tons. This indicates a significant industrial scale of production.

What is the industrial process for producing Prenol?

Industrially, Prenol is produced by reacting formaldehyde with isobutene to form isoprenol (3-methyl-3-buten-1-ol), which is then isomerized to yield Prenol (3-methyl-2-buten-1-ol). This multi-step synthesis is a common method for producing this chemical.

What is the role of isoprenol in Prenol's industrial production?

Isoprenol, specifically 3-methyl-3-buten-1-ol, is an intermediate product in the industrial synthesis of Prenol. It is formed first from the reaction of isobutene and formaldehyde, and then isomerized into Prenol.

What is the primary use of Prenol in industrial applications?

Prenol is primarily used as a precursor for the industrial production of citral. Citral, in turn, is an important intermediate in the synthesis of vitamins A, E, and K.

What aldehyde is produced when Prenol is oxidized?

When Prenol is oxidized, it produces the aldehyde known as prenal. This aldehyde is a key step in the pathway to synthesizing citral.

What are isoprenoid alcohols, and what is their general formula?

Isoprenoid alcohols are compounds built from repeating isoprene units. Their general formula is H–[CH₂CCH₃=CHCH₂]n–OH, where the repeating C₅H₈ unit is derived from isoprene. Prenol itself is the simplest example of such a structure.

How does Prenol relate to the concept of 'isoprenols'?

Prenol is considered one of the simplest terpenoids and is a building block for isoprenoid alcohols, which are sometimes referred to as 'isoprenols' due to their structural relation to isoprene units. However, it's important not to confuse Prenol with its isomer, isoprenol (3-methyl-3-buten-1-ol).

What are some examples of isoprenoid alcohols with different chain lengths?

Examples of isoprenoid alcohols include geraniol (n=2), farnesol (n=3), and geranylgeraniol (n=4). These compounds differ in the number of isoprene units linked together.

What are dolichols, and how do they differ from isoprenoid alcohols like Prenol?

Dolichols are isoprenoid alcohols where the isoprene unit attached to the alcohol group is saturated (meaning it contains no double bonds). They are distinct from unsaturated isoprenoid alcohols like Prenol and its derivatives.

What is the biological significance of dolichols?

Dolichols play crucial roles in biological processes, serving as glycosyl carriers in the synthesis of polysaccharides. They also help protect cellular membranes, stabilize cell proteins, and support the immune system.

How are polyprenols formed, and what is their general structure?

Polyprenols are formed through dehydration reactions involving prenol, resulting in polymers with at least five isoprene units (n ≥ 5 in the general formula H–[CH₂CCH₃=CHCH₂]n–OH). These long-chain alcohols, also called 'terpenols', retain a hydroxyl group at one end and can contain up to 100 isoprene units.

What roles do polyprenols and related long-chain isoprenoid alcohols play in biological systems?

These long-chain isoprenoid alcohols, including polyprenols, are important in the acylation of proteins, carotenoids, and fat-soluble vitamins such as A, E, and K. They are also involved in cell metabolism.

What is the significance of ingested polyprenols for human and animal health?

Ingested polyprenols are metabolized by the liver into dolichols, which can then participate in the dolichol phosphate cycle and be assimilated by the body. This process is thought to be beneficial, particularly in cases of dolichol deficits associated with inflammatory, degenerative, or oncological diseases.

What is a readily available natural source for extracting polyprenols?

Live conifer needles are identified as one of the richest and most widely available natural sources for extracting polyprenols. Commercial extraction methods are designed to preserve the biological activity of these compounds.

How does the flash point of Prenol relate to its safety classification?

While there might be slight variations in reported flash points (e.g., 43.3 °C vs. 51.5 °C), the value consistently classifies Prenol as a flammable liquid. For instance, it falls under GHS category 3 for flammable liquids and is considered a Class II combustible liquid in the US, indicating it requires careful handling to prevent fire hazards.

What does the image labeled 'Skeletal formula of prenol' depict?

The image labeled 'Skeletal formula of prenol' displays a simplified representation of the Prenol molecule's chemical structure, showing the arrangement of carbon and oxygen atoms and their bonds without explicitly drawing all hydrogen atoms.

What information is conveyed by the 'Ball-and-stick model' image of Prenol?

The 'Ball-and-stick model' image provides a three-dimensional representation of Prenol, illustrating how the atoms are connected and their relative positions in space, which helps in understanding the molecule's shape.

What chemical reaction is illustrated in the image titled 'The reaction of isobutene with formaldehyde to give isoprenol'?

The image titled 'The reaction of isobutene with formaldehyde to give isoprenol' visually represents the initial step in the industrial production of Prenol, showing how isobutene and formaldehyde combine to form the intermediate compound isoprenol.

What chemical transformation is shown in the image titled 'The isomerization of isoprenol to prenol'?

The image titled 'The isomerization of isoprenol to prenol' depicts the second step in the industrial synthesis of Prenol, illustrating the chemical rearrangement of isoprenol into Prenol.

Prenol Wiki: Prenol: Nature's Versatile Terpenoid Alcohol

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About Prenol

Chemical Identity

Prenol, systematically named 3-methyl-2-buten-1-ol, is a naturally occurring organic compound classified as a simple alcohol. It represents one of the most basic structures within the broader class of terpenoids.

Physical Characteristics

This compound presents as a clear, colorless oil at standard conditions. It exhibits moderate solubility in water and is fully miscible with most common organic solvents, facilitating its use in various chemical processes.

Sensory Profile

Prenol possesses a distinct fruity aroma, which lends itself to applications in the fragrance industry, albeit occasionally. Its olfactory properties contribute to the complex scent profiles of various natural sources.

Natural Occurrence

Found in Nature

Prenol is a widespread natural product, identified in numerous fruits and plants. Its presence has been documented in citrus fruits, cranberry, bilberry, currants, raspberries, blackberries, and tomatoes. It is also found in trace amounts in hop oil, coffee, and various berries like arctic bramble and cloudberry, as well as passion fruit.

Chemical Properties

Key Identifiers and Data

Prenol is characterized by several key identifiers and physical properties crucial for its identification and application:

Names

Preferred IUPAC name: 3-Methylbut-2-en-1-ol

Other names: 3,3-Dimethylallyl alcohol

Identifiers

CAS Number: 556-82-1

ChEBI: CHEBI:16019

ChemSpider: 10700

ECHA InfoCard: 100.008.312

EC Number: 209-141-4

PubChem CID: 11173

UNII: 55MY0HM445

CompTox EPA: DTXSID2027206

InChI: 1S/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3

InChIKey: ASUAYTHWZCLXAN-UHFFFAOYSA-N

SMILES: OC\C=C(/C)C

Properties

Chemical formula: C₅H₁₀O

Molar mass: 86.132 g/mol

Density: 0.848 g/cm³

Melting point: −59 °C (−74 °F; 214 K) (calculated)

Boiling point: 142 °C (288 °F; 415 K) (approximation)

Solubility in water: 17 g/100 ml (at 20 °C)

log P: 0.91

Vapor pressure: 3.17 hPa (at 25 °C, extrapolated)

Safety and Hazards

GHS Classification

Prenol is classified under the Globally Harmonized System (GHS) with specific hazard indicators:

Pictograms: 🔥 ❗

Signal word: Warning

Hazard statements: H226, H302

Precautionary statements: P210, P233, P240, P241, P242, P243, P264, P270, P301+P312, P303+P361+P353, P330, P370+P378, P403+P235, P501

Flash point: 43.3 °C (109.9 °F; 316.4 K)

Industrial Production

Synthesis Pathway

Industrially, Prenol is synthesized through a multi-step process. Initially, isobutene reacts with formaldehyde. This reaction yields isoprenol (3-methyl-3-buten-1-ol). Subsequently, isoprenol undergoes isomerization to produce Prenol (3-methyl-2-buten-1-ol).

Major manufacturers include BASF in Germany and Kuraray in Asia, highlighting its global industrial significance.

Applications and Uses

Chemical Intermediate

Prenol serves primarily as a crucial precursor in the industrial synthesis of citral. Citral is a key intermediate compound used in the production of essential vitamins, including Vitamin A, Vitamin E, and Vitamin K. The process involves the oxidation of Prenol to its corresponding aldehyde, prenal.

Fragrance Component

Due to its characteristic fruity aroma, Prenol finds occasional use in the formulation of fragrances, contributing subtle notes to complex scent compositions.

Role in Polymer Chemistry

Building Block for Isoprenoids

Prenol is a fundamental unit in the synthesis of isoprenoid alcohols, which are characterized by repeating C₅H₈ isoprene moieties. These compounds are sometimes referred to as 'isoprenols', though this should not be confused with the isomer isoprenol (3-methyl-3-buten-1-ol).

When these isoprenoid units are linked end-to-end, particularly when saturated, they form compounds known as polyprenols. These long-chain alcohols can consist of numerous isoprene units (up to 100) and play significant roles in biological processes:

Dolichols: Saturated isoprenoid alcohols are termed dolichols. They function as crucial glycosyl carriers in the synthesis of polysaccharides and are vital for stabilizing cellular membranes, protecting proteins, and supporting the immune system.
Polyprenols: Unsaturated long-chain isoprenoid alcohols are called polyprenols. They are involved in the acylation of proteins, carotenoids, and fat-soluble vitamins (A, E, K).
Metabolic Significance: Polyprenols are implicated in cell metabolism. Research suggests that ingested polyprenols can be converted into dolichols in the liver, participating in the dolichol phosphate cycle. This pathway is relevant in conditions involving dolichol deficits, such as chronic inflammatory, degenerative, and oncological diseases.
Natural Sources: Conifer needles are recognized as a particularly rich source for polyprenol extraction, utilizing gentle methods to preserve biological activity.

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References

A full list of references for this article are available at the Prenol Wikipedia page

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This page was generated by an Artificial Intelligence and is intended for informational and educational purposes only. The content is derived from a snapshot of publicly available data and may not be entirely accurate, complete, or up-to-date.

This is not professional chemical or safety advice. The information provided herein is not a substitute for expert consultation regarding chemical properties, handling, safety, or industrial applications. Always refer to official safety data sheets (SDS), technical documentation, and consult with qualified chemical professionals for specific requirements and guidance. Never disregard professional advice or delay in seeking it because of information presented on this website.

The creators of this page are not responsible for any errors or omissions, or for any actions taken based on the information provided.

Prenol: Nature's Versatile Terpenoid Alcohol

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About Prenol 🌿

🧬 Chemical Identity

💧 Physical Characteristics

👃 Sensory Profile

Natural Occurrence 🌍

🍎 Found in Nature

Chemical Properties 🔬

📊 Key Identifiers and Data

Names

Identifiers

Properties

Safety and Hazards ⚠️

🔥 GHS Classification

Industrial Production 🏭

⚙️ Synthesis Pathway

Applications and Uses 💡

💊 Chemical Intermediate

✨ Fragrance Component

Role in Polymer Chemistry 🔗

🧱 Building Block for Isoprenoids

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About Prenol

Chemical Identity

Physical Characteristics

Sensory Profile

Natural Occurrence

Found in Nature

Chemical Properties

Key Identifiers and Data

Safety and Hazards

GHS Classification

Industrial Production

Synthesis Pathway

Applications and Uses

Chemical Intermediate

Fragrance Component

Role in Polymer Chemistry

Building Block for Isoprenoids

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