What is another name for allicin?

When a clove of garlic is crushed, the enzyme alliinase rapidly converts the odorless alliin into the potent-smelling organosulfur compound allicin. This highly reactive substance is known by several other names, including its chemical and systematic identifiers.

Quick Summary

The compound allicin, prominent in crushed garlic, is also known by its chemical name diallyl thiosulfinate. It is an unstable and highly reactive organosulfur compound responsible for garlic's characteristic pungent odor and many of its biological activities.

Key Points

• Diallyl Thiosulfinate: This is the most common chemical name and a primary alternative name for allicin.

• IUPAC Name: The systematic chemical name is S-(prop-2-en-1-yl) prop-2-ene-1-sulfinothioate.

• Enzymatic Reaction: Allicin is created when the enzyme alliinase acts on the precursor alliin in crushed garlic.

• Unstable Nature: This compound is highly unstable and readily decomposes, especially when heated.

• Source of Pungency: Allicin is directly responsible for the pungent aroma of freshly crushed garlic.

• Formation of Other Compounds: As it degrades, allicin forms other sulfur compounds like ajoene and diallyl polysulfides.

• Health Benefits: The biological activity and health benefits associated with garlic, such as antimicrobial and antioxidant effects, are largely attributed to allicin's reactivity.

• Supplement Factors: The effectiveness of garlic supplements depends on their ability to form and release allicin or its bioactive derivatives.

Another Name for Allicin: Diallyl Thiosulfinate

The most common alternative name for allicin is diallyl thiosulfinate. This name refers to the chemical structure of the compound, which features two allyl groups linked by a thiosulfinate functional group. The International Union of Pure and Applied Chemistry (IUPAC) also provides a more technical, systematic name for allicin: S-(prop-2-en-1-yl) prop-2-ene-1-sulfinothioate. While these formal chemical names are precise, diallyl thiosulfinate is widely recognized in scientific and health circles as a direct synonym for allicin.

The Chemistry of Allicin: Formation and Instability

Allicin is not present in an intact garlic bulb but is formed when the tissue is damaged through chopping, crushing, or chewing. This mechanical process breaks open cell compartments, allowing the enzyme alliinase to interact with the stable precursor compound, alliin (S-allyl-L-cysteine sulfoxide). This reaction triggers the rapid conversion that produces allicin and is responsible for the distinct, pungent smell of freshly prepared garlic.

However, allicin is an unstable compound and quickly breaks down at room temperature. It degrades into a number of other beneficial organosulfur compounds, such as diallyl disulfide (DADS), diallyl trisulfide (DATS), and ajoene. This process explains why the pungent smell of crushed garlic changes over time and why the effects can differ depending on whether garlic is consumed raw or cooked. Heat also accelerates the decomposition of allicin, which is why cooked garlic has a milder flavor compared to raw garlic.

Therapeutic Potential and Biological Activity

Allicin and its breakdown products have been the subject of extensive research for their potential health benefits, including potent antimicrobial, antioxidant, and anti-inflammatory properties. The compound's high reactivity with thiol groups found in proteins is believed to be the basis for many of these biological activities. This interaction allows allicin to interfere with key metabolic processes in various microorganisms, making it a natural antimicrobial agent.

Key Biological Effects of Allicin

• Antimicrobial Action: Allicin and its derivatives are effective against a broad spectrum of bacteria, fungi, and viruses, including antibiotic-resistant strains.
• Antioxidant Effects: Through its ability to react with thiols and modulate cellular redox potential, allicin can help protect the body from oxidative stress.
• Cardiovascular Support: Research indicates that allicin may help support cardiovascular health by reducing blood pressure and cholesterol levels.
• Anti-inflammatory Properties: The compound has been shown to exhibit anti-inflammatory effects by influencing cellular signaling pathways.

A Comparison of Allicin's Names and Properties

Feature	Allicin	Diallyl Thiosulfinate	S-(prop-2-en-1-yl) prop-2-ene-1-sulfinothioate
Classification	Common name	Chemical name	IUPAC name
Description	Naturally occurring, reactive compound in garlic.	Identifies the compound's chemical structure.	The most systematic and precise chemical name.
Source	Produced from crushed or chopped garlic.	Not a source, but a name describing the compound.	Not a source, but a formal chemical identifier.
Stability	Very unstable; decomposes rapidly.	Inherently refers to the unstable compound itself.	Refers to the unstable molecule, not its stability.
Use Case	General reference in health articles and supplements.	Used in chemical and scientific contexts.	Primary use in highly technical chemical literature.

Practical Implications for Health and Supplements

The inherent instability of allicin has significant implications for both culinary use and dietary supplements. To maximize allicin content, fresh garlic should be chopped or crushed and allowed to sit for several minutes before adding to heat. For supplements, the dosage and effectiveness can vary widely depending on how the product is manufactured and whether it can effectively release allicin. Some supplements are enteric-coated to prevent the enzyme alliinase from being inactivated by stomach acid, ensuring allicin is formed in the intestines.

Conclusion

In summary, the most widely recognized alternative name for allicin is diallyl thiosulfinate. While more complex systematic names like S-(prop-2-en-1-yl) prop-2-ene-1-sulfinothioate exist, diallyl thiosulfinate is the most common chemical synonym used in both scientific and popular contexts. Understanding that allicin is actually produced upon damage to the garlic clove, and that it is an unstable but highly bioactive compound, is key to appreciating its role in the health benefits associated with garlic.

References

• Allicin Structure, Chemical Formula & Properties - Study.com
• Allicin: Chemistry and Biological Properties - PMC
• Allicin - Wikipedia
• Allicin - American Chemical Society
• Chemical Constituents and Pharmacological Activities of Garlic (Allium sativum L.) - PMC
• How Allicin Might Boost Your Health Naturally - Verywell Health
• allicin, 539-86-6 - The Good Scents Company
• Allicin Bioavailability and Bioequivalence from Garlic Supplements and Foods - PMC
• Garlic: An Exploration of Allicin and Antioxidant Activity - Nutrition Therapy Institute
• CAS 539-86-6: Allicin - CymitQuimica

How Allicin is Formed

When a garlic clove is crushed or chopped, the enzyme alliinase reacts with the precursor compound alliin to produce allicin, a process that happens very quickly.

The Instability of Allicin

Allicin is highly volatile and unstable, decomposing at room temperature into a range of other sulfur compounds such as ajoene, diallyl disulfide (DADS), and diallyl trisulfide (DATS).

Health Properties of Allicin

Allicin and its degradation products are associated with numerous health benefits, including antimicrobial, antioxidant, and anti-inflammatory effects.

Using Garlic for Allicin Content

To maximize allicin production, it is best to crush or chop fresh garlic and let it sit for several minutes before applying heat, as cooking accelerates the breakdown of allicin.

Supplement Considerations

For dietary supplements, the bioavailability and effectiveness of allicin can vary significantly, with some products using enteric coatings to protect the alliinase enzyme from stomach acid.

Allicin and Body Odor

The sulfur compounds derived from allicin metabolism are responsible for the characteristic garlic odor that can be excreted through the breath and skin.

Why Raw Garlic is More Potent

Raw garlic contains the enzyme alliinase which, upon crushing, generates allicin. Cooking inactivates this enzyme, thus reducing the formation of allicin.

Conclusion: The Name Behind the Pungency

The most common and descriptive alternative name for allicin is diallyl thiosulfinate. This powerful yet unstable compound is central to the chemical processes that give garlic its signature flavor and many of its therapeutic effects. The creation and degradation of allicin highlight the dynamic chemistry of garlic and influence its optimal preparation for both culinary and medicinal purposes.

Key Takeaways About Allicin's Name and Chemistry

• Other Name: Allicin is also known as diallyl thiosulfinate, its chemical name.
• Garlic's Defense: It is a defense molecule produced by garlic when the plant's tissue is damaged.
• Biosynthesis: Allicin is formed when alliin and the enzyme alliinase mix after a garlic clove is crushed or chopped.
• Instability: It is an unstable compound that quickly breaks down, especially with heat.
• Further Compounds: The breakdown of allicin leads to other organosulfur compounds like ajoene and diallyl disulfides.
• Biological Activity: Its health benefits, including antimicrobial and antioxidant effects, are primarily due to its reactivity with thiol-containing proteins.
• Bioavailability: Allicin's instability affects its bioavailability in supplements, which sometimes use enteric coatings for protection.
• Odor Source: The strong odor of crushed garlic is a direct result of allicin's formation.

Frequently Asked Questions

What is the scientific name for allicin?

The scientific or chemical name for allicin is diallyl thiosulfinate. More formally, according to the IUPAC system, it can be named S-(prop-2-en-1-yl) prop-2-ene-1-sulfinothioate.

How is allicin formed in garlic?

Allicin is not present in whole, undamaged garlic. It is formed when the garlic is crushed, chopped, or chewed, which causes the enzyme alliinase to react with the compound alliin, triggering the conversion that produces allicin.

Why is it important to let crushed garlic sit?

Allowing crushed garlic to sit for a few minutes before cooking maximizes the production of allicin through the enzymatic reaction. Cooking inactivates the alliinase enzyme, so pre-chopping gives the reaction time to occur.

Does allicin survive cooking?

Allicin is highly unstable and breaks down rapidly when exposed to heat, which is why cooked garlic has a milder flavor and less pungency. This degradation process converts allicin into a variety of other, more stable, organosulfur compounds.

What happens to allicin in the body?

After ingestion, allicin is quickly metabolized. It reacts with thiol groups in the body and is broken down into various compounds, including allyl mercaptan, which is then further metabolized to allyl methyl sulfide (AMS).

Why do some garlic supplements use an enteric coating?

The enteric coating is used to protect the alliinase enzyme from being destroyed by acidic stomach conditions. This allows the supplement to pass through the stomach and release the alliinase in the intestine, where it can produce allicin.

What are the health benefits of allicin?

Allicin is known for its antibacterial and antifungal properties, as well as its antioxidant and anti-inflammatory effects. It also has been studied for its potential cardiovascular benefits.