Resveratrol (Trans-Resveratrol)

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Resveratrol

Resveratrol:This Week’s Trans-Form Molecule

Resveratrol was first obtained from white hellebore (Veratum grandiflorum). Its benefits have long been recognized only after the so-called French paradox (associated with frequent drinking of red wine) was publicized. It was believed that resveratrol can prevent cardiovascular diseases in several ways. Resveratrol is an antioxidant. Some studies have shown that it is helpful in protecting your cells from free radicals causing damage, lowering of blood pressure, improving the integrity of blood vessels and preventing risk of neurodegenerative diseases such as Alzheimer's disease. With all this being said, many times people get confused or simply do not know about the isomers of Resveratrol.

The Chemistry of Resveratrol

Resveratrol can exist in two forms, Trans-Resveratrol and Cis-Resveratrol. Both forms contains the same amount and type of atoms but simply positioned differently. Think of this like:

1+2= 3

2+1= 3

Both formula contains 1 and 2 which is equal to 3 but simply positioned differently. The chemistry behind the type of isomer will however yield a different result. Cis-Resveratrol was proved to be very unstable and not easily absorbed in the body, while Trans-Resveratrol was proved to be stable and easily absorbed throughout the body. The ease of absorption will therefore yield different results between the two. In conclusion, when people speak about the benefits of Resveratrol, they are making reference to Trans-Resveratrol.

Resveratrol Cis vs Trans

Now, since we’ve differentiated the 2 we will be focusing on building Trans-Resveratrol!

What does Trans-Resveratrol look like in Chemistry?

Resveratrol stillbenoid
Resveratrol molecular model

Let’s Get Building!

Get your Student Molecular Model Set from Duluth Labs then let’s create Resveratrol! You’ll need:

  • 14 Carbon Atoms

  • 3 Oxygen Atoms

  • 12 Hydrogen

  • 12 Small connectors (compact short bonds for hydrogen)

  • 11 Medium connectors (single covalent bonds)

  • 14 Long connectors

  • Molecular Tool (for Disassembly)

Put aside all the atoms and connectors needed.

Note: We will build the first benzene ring (see leftmost portion of resveratrol molecule) in a clockwise rotation, starting with the 12:00 position (Carbon 3). Kindly refer to the structure above.

Steps

  • 1
    Resveratrol molecular model

    1. First, get one carbon atom (Carbon 3), then attach another carbon atom (Carbon 2) to it using 2 long connectors connector. Add a hydrogen atom to carbon 2 using a small connector.

  • 2
    Resveratrol molecular model

    2. Attach another carbon atom (Carbon 1) below Carbon 2 using a medium connector.

  • 3
    Resveratrol molecular model

    3. Then using 2 long connectors, attach another carbon atom (Carbon 6) to Carbon 1. Place a hydrogen atom on Carbon 6 using a small connector.

  • 4
    Resveratrol molecular model

    4. Get another carbon atom (Carbon 5) then attach this to Carbon 6 using a medium connector.

  • 5
    Resveratrol molecular model

    5. Using a medium connector, attach one Oxygen atom to Carbon 5. Then, using a small connector, add a hydrogen atom to this oxygen.

  • 6
    Resveratrol molecular model

    6. Connect another carbon atom (Carbon 4) to Carbon 5 using 2 long connectors. Then add a hydrogen atom on Carbon 4 using a small connector.

  • 7
    Resveratrol molecular model

    7. Use a medium connector to join Carbon 4 and Carbon 3 together.

  • 8
    Resveratrol molecular model

    8. Now get an Oxygen atom and attach it to Carbon 3 using 1 medium connector. Then, add a hydrogen atom on this oxygen using a small connector.

  • Resveratrol molecular model

    Excellent! We are now done with building the first aromatic benzene ring of our resveratrol.

Note: We will now proceed with building the second benzene ring (see rightmost portion of the resveratrol molecule below. In this portion of our molecule, we start with Carbon 6’, then we will continue building it in a clockwise direction. Let’s continue!

Trans-Resveratrol

Steps

  • 1
    Resveratrol molecular model

    1. Get a carbon atom (Carbon 6’) then add 1 hydrogen atom to it using a small connector.

  • 2
    Resveratrol molecular model

    2. Attach another carbon (Carbon 5’) to the right of Carbon 6’ using 2 long connectors. Then add a hydrogen atom to Carbon 5’ using a small connector.

  • 3
    Resveratrol molecular model

    3. Then, using a medium connector, attach a carbon atom (Carbon 4’) below Carbon 5’.

  • 4
    Resveratrol molecular model

    4. Use a medium connector to attach an Oxygen atom to Carbon 4’. Then add a hydrogen atom to this oxygen using a small connector.

  • 5
    Resveratrol molecular model

    5. Attach another carbon (Carbon 3’) to Carbon 4’ using 2 long connectors, then place one hydrogen atom on Carbon 3’ with a small connector.

  • 6
    Resveratrol molecular model

    6. Attach another carbon atom (Carbon 2’) to Carbon 3’ using a medium connector. Then, place a hydrogen atom on Carbon 2’ using a short connector.

  • 7
    Resveratrol molecular model

    7. Get another carbon atom (Carbon 1’) and attach this above Carbon 2’ using 2 long connectors.

  • 8
    Resveratrol molecular model

    8. Join Carbon 1’ and Carbon 6’ together using a medium connector.

  • Resveratrol molecular model

    Hooray! We now have our two aromatic rings.

Note: We have to join these two molecules with an ethenyl (or vinyl) molecule Let’s begin!

Resveratrol stilbenoid

Steps

  • 1
    Resveratrol molecular model

    1. Using a carbon atom, and attach this to another carbon using 2 long connectors. You now have your ethenyl molecule!

  • 2
    Resveratrol molecular model

    2. Now, attach one Carbon of your ethenyl molecule to Carbon 1 of your first aromatic ring (aromatic ring with 2 hydroxyl groups) using a medium connector. Also attach a hydrogen atom on the ethenyl group using a short connector.

  • 3
    Resveratrol molecular model

    3. Lastly, attach the other Carbon of ethenyl molecule to Carbon 1’ of your second aromatic ring (aromatic ring with 1 hydroxyl group) using a medium connector. Then use a short connector to attach another hydrogen atom to the ethenyl group.

There you have it! We’ve just built another molecule – Resveratrol!

We hope to see how your Resveratrol molecule turned out!


Comment and share pictures below! Tune in next week for another molecule of the week! See you then xoxo :)

 

Duluth Labs

Afton Direct LLC


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