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STEREOCHEMICAL THEORY OF
       OLFACTION
The Stereochemical theory of olfaction states
that a molecule's particular smell is due to a 'lock
and key' mechanism by which a scent molecule
fits into olfactory receptors in the nasal epithelium.


Stereochemistry, a subdiscipline of chemistry, involves the study
of the relative spatial arrangement of atoms that form the structure
of molecules and their manipulation. An important branch of
stereochemistry is the study of chiral molecules.
Stereochemistry is also known as 3D chemistry because the prefix
"stereo-" means "three-dimensionality".
The study of Stereochemistry focuses on stereoisomers.
stereoisomers.are isomeric molecules that have the same
molecular formula and sequence of bonded atoms (constitution),
but that differ only in the three-dimensional orientations of their
atoms in space. This contrasts with structural isomers, which share
the same molecular formula, but the bond connections and/or their
order differ(s) between different atoms/groups. In stereoisomers,
the order and bond connections of theconstituent atoms remain the
same, but their orientation in space differs


There are 2 types of stereoisomers:
ENANTIOMERS
In chemistry, an enantiomer is one of two stereoisomers that are
mirror images of each other that are non-superposable (not
identical), much as one's left and right hands are the same except
for opposite orientation.
S-lactic acid and L-lactic acid
Chirality
A chiral molecule is a type of molecule that has a non-
superposable mirror image. The feature that is most often the cause
of chirality in molecules is the presence of an asymmetric carbon
atom.
In chemistry, chirality usually refers to molecules. Two mirror
images of a chiral molecule are called enantiomers or optical
isomers.




Diastereomer:
Diastereomers (sometimes called diastereoisomers) are
stereoisomers that are not enantiomers. Diastereomerism occurs
when two or more stereoisomers of a compound have different
configurations at one or more (but not all) of the equivalent
(related) stereocenters and are not mirror images of each other




.           L-tartaric acid
D-tartaric acid




                        DIASTEREOMERS

Olfaction is the sense of smell. This sense is mediated by
specialized sensory cells of the nasal cavity of vertebrates, and, by
sensory cells of the antennae of invertebrates.
OLFACTION depends on the structure of particular molecule.
Human olfactory system. 1: Olfactory bulb 2: Mitral cells 3:
Bone 4: Nasal epithelium 5: Glomerulus (olfaction) 6:
Olfactory receptor cells



Detection of odors
  1.The initial detection of odors takes place at the back of the
    nose in a small region known as the olfactory epithelium.
  2.Dissolved molecules interact with specialized receptors called
    odorant-binding proteins. (Odorants are molecules that
    stimulate the olfactory receptors.)
3.The binding of the molecules to these receptors initiate an
    electrical signal that transmits to the olfactory bulbs and
    higher brain centers for processing of the olfactory
    information.
  4.To distinguish the smell, the brain must then determine
    the precise combination of receptors that are activated
    by a particular odor.




SO, olfactiondepends on the structure of particular molecule.




Odorants must be volatile

Odorants are nonionic compounds,It must be volatile at
ambient temperature, so that the molecule can reach the
nose. It must interact with the protein odorant receptor
sites in the nose.
VOLATILE OILS

Volatile oils are the odorous principles found in
various plant parts.




    STEREOISOMERS, VOLATILE OILS AND
    OLFACTION:

    1.




                   (VOLATILE OIL)
         STEREOISOMER(CONSTITUENT OF Orange
                      and Lemon)
                    Smells differently
2.




     (VOLATILE OIL)(+ )Carvone smells like Mint and(-
             )Carvone smells like Caraway




3.One stereoisomers of PHENANDRENE smells
likeeucalyptus andother smell likefennel.




                α-Phellandrene(Smells like Eucalyptus)




              β-phellandrene(smells like fennel)

Because molecules of volatile oils bind to specific proteins
in nasal cavity called olfactory receptors .Each olfactory
receptor can only bind molecules that have a
complementary shape, just as right hand will only fit into
a right-handed glove, and that's how brain distinguishes
between the scent of the the two stereoisomer molecules
bind to olfactory receptors on different nerve endings in
nose.

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Stereochemical theory of olfaction.docx 1

  • 1. STEREOCHEMICAL THEORY OF OLFACTION The Stereochemical theory of olfaction states that a molecule's particular smell is due to a 'lock and key' mechanism by which a scent molecule fits into olfactory receptors in the nasal epithelium. Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms that form the structure of molecules and their manipulation. An important branch of stereochemistry is the study of chiral molecules. Stereochemistry is also known as 3D chemistry because the prefix "stereo-" means "three-dimensionality". The study of Stereochemistry focuses on stereoisomers. stereoisomers.are isomeric molecules that have the same molecular formula and sequence of bonded atoms (constitution), but that differ only in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections and/or their order differ(s) between different atoms/groups. In stereoisomers, the order and bond connections of theconstituent atoms remain the same, but their orientation in space differs There are 2 types of stereoisomers:
  • 2. ENANTIOMERS In chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable (not identical), much as one's left and right hands are the same except for opposite orientation.
  • 3. S-lactic acid and L-lactic acid Chirality A chiral molecule is a type of molecule that has a non- superposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom. In chemistry, chirality usually refers to molecules. Two mirror images of a chiral molecule are called enantiomers or optical isomers. Diastereomer: Diastereomers (sometimes called diastereoisomers) are stereoisomers that are not enantiomers. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent (related) stereocenters and are not mirror images of each other . L-tartaric acid
  • 4. D-tartaric acid DIASTEREOMERS Olfaction is the sense of smell. This sense is mediated by specialized sensory cells of the nasal cavity of vertebrates, and, by sensory cells of the antennae of invertebrates. OLFACTION depends on the structure of particular molecule.
  • 5. Human olfactory system. 1: Olfactory bulb 2: Mitral cells 3: Bone 4: Nasal epithelium 5: Glomerulus (olfaction) 6: Olfactory receptor cells Detection of odors 1.The initial detection of odors takes place at the back of the nose in a small region known as the olfactory epithelium. 2.Dissolved molecules interact with specialized receptors called odorant-binding proteins. (Odorants are molecules that stimulate the olfactory receptors.)
  • 6. 3.The binding of the molecules to these receptors initiate an electrical signal that transmits to the olfactory bulbs and higher brain centers for processing of the olfactory information. 4.To distinguish the smell, the brain must then determine the precise combination of receptors that are activated by a particular odor. SO, olfactiondepends on the structure of particular molecule. Odorants must be volatile Odorants are nonionic compounds,It must be volatile at ambient temperature, so that the molecule can reach the nose. It must interact with the protein odorant receptor sites in the nose.
  • 7. VOLATILE OILS Volatile oils are the odorous principles found in various plant parts. STEREOISOMERS, VOLATILE OILS AND OLFACTION: 1. (VOLATILE OIL) STEREOISOMER(CONSTITUENT OF Orange and Lemon) Smells differently
  • 8. 2. (VOLATILE OIL)(+ )Carvone smells like Mint and(- )Carvone smells like Caraway 3.One stereoisomers of PHENANDRENE smells likeeucalyptus andother smell likefennel. α-Phellandrene(Smells like Eucalyptus) β-phellandrene(smells like fennel) Because molecules of volatile oils bind to specific proteins in nasal cavity called olfactory receptors .Each olfactory
  • 9. receptor can only bind molecules that have a complementary shape, just as right hand will only fit into a right-handed glove, and that's how brain distinguishes between the scent of the the two stereoisomer molecules bind to olfactory receptors on different nerve endings in nose.