Tyrosinol

Last updated
Tyrosinol
Tyrosinol.svg
Names
Other names
β-amino-4-hydroxybenzenepropanol
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C9H13NO2/c10-8(6-11)5-7-1-3-9(12)4-2-7/h1-4,8,11-12H,5-6,10H2
    Key: DBLDQZASZZMNSL-UHFFFAOYSA-N
  • (L-):InChI=1S/C9H13NO2/c10-8(6-11)5-7-1-3-9(12)4-2-7/h1-4,8,11-12H,5-6,10H2/t8-/m0/s1
    Key: DBLDQZASZZMNSL-QMMMGPOBSA-N
  • (D-):InChI=1S/C9H13NO2/c10-8(6-11)5-7-1-3-9(12)4-2-7/h1-4,8,11-12H,5-6,10H2/t8-/m1/s1
    Key: DBLDQZASZZMNSL-MRVPVSSYSA-N
  • C(C(CO)N)C1=CC=C(O)C=C1
  • (L-):C1=CC(=CC=C1C[C@@H](CO)N)O
  • (D-):C1=CC(=CC=C1C[C@H](CO)N)O
Properties
C9H13NO2
Molar mass 167.208 g·mol−1
Appearancewhite solid
Melting point 91.4–92.1 °C (196.5–197.8 °F; 364.5–365.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tyrosinol is an organic compound with the formula HOC6H4CH2CH(NH2)CH2OH. A colorless or white solid, it is produced by the reduction of the amino acid tyrosine with borane dimethylsulfide. [1] The compound, which is chiral, is an example of a 1,2-ethanolamine as well as a phenethylamine. [2]

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In chemistry, a racemic mixture or racemate, is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates.

<span class="mw-page-title-main">Enantiomer</span> Stereoisomers which are non-superposable mirror images of each other

In chemistry, an enantiomer – also called optical isomer, antipode, or optical antipode – is one of two stereoisomers that are non-superposable onto their own mirror image. Enantiomers are much like one's right and left hands; without mirroring one of them, hands cannot be superposed onto each other. No amount of reorientation in three spatial dimensions will allow the four unique groups on the chiral carbon to line up exactly. The number of stereoisomers a molecule has can be determined by the number of chiral carbons it has. Stereoisomers include both enantiomers and diastereomers.

<span class="mw-page-title-main">Stereocenter</span> Atom which is the focus of stereoisomerism in a molecule

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2
CH
2
NH
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or C
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7
NO
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In chemistry, a molecule or ion is called chiral if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality. The terms are derived from Ancient Greek χείρ (cheir) 'hand'; which is the canonical example of an object with this property.

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References

  1. Phoon, Chee Wee; Abell, Chris (1998). "Solid Phase Aldol and Conjugate Addition Reactions Using Evans' Oxazolidinone Chiral Auxiliary". Tetrahedron Letters. 39 (17): 2655–2658. doi:10.1016/S0040-4039(98)00230-5.
  2. Martin Ernst; Johann-Peter Melder; Franz Ingo Berger; Christian Koch (2022). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001.pub2. ISBN   978-3527306732.