Interesting facts
Exploring (2R)-2-Hydroxy-2-phenyl-acetic acid
(2R)-2-hydroxy-2-phenyl-acetic acid, also known as mandelic acid, is a fascinating compound that offers valuable insights into both organic chemistry and medicinal applications. This compound is notable for its chiral nature, as the (2R) prefix indicates that it exists in a specific stereochemical configuration. Its significance can be appreciated in several ways:
- Pharmaceutical Applications: Mandelic acid has a history of use in the treatment of urinary tract infections. It is effective against various bacterial strains and has been a staple in certain antibiotic therapies.
- Dermatological Uses: In skincare, mandelic acid is revered for its exfoliating properties. It belongs to the alpha-hydroxy acid (AHA) family, which is known to improve skin texture and treat acne.
- Synthesis in Organic Chemistry: The compound can be synthesized through various methods, showcasing pathways such as the hydrolysis of benzalacetone or through the reaction of phenylacetaldehyde with cyanide.
- Chirality and Its Implications: The (2R) designation means that only one enantiomer exhibits significant biological activity. This is a prime example of how chirality plays a critical role in pharmacology and drug design.
- Research Potential: With ongoing studies exploring its anti-inflammatory and analgesic effects, this compound continues to inspire research in medicinal chemistry.
In the words of famous chemist Linus Pauling, “The best way to have a good idea is to have lots of ideas.” (2R)-2-hydroxy-2-phenyl-acetic acid serves as a reminder of the importance of exploring different compounds for innovative solutions in medicine and beyond.
As we delve deeper into the world of molecular structure and functionality, compounds like mandelic acid highlight the intricate balance between chemistry and its real-world applications.
Synonyms
611-71-2
(R)-(-)-Mandelic acid
(r)-mandelic acid
(R)-2-Hydroxy-2-phenylacetic acid
D-(-)-MANDELIC ACID
D-Mandelic acid
(-)-Mandelic acid
D(-)-Mandelic acid
(2R)-2-hydroxy-2-phenylacetic acid
Mandelic acid, (R)-
D-2-Phenylglycolic acid
(-)-(R)-Mandelic acid
(R)-alpha-Hydroxyphenylacetic acid
R-(-)-Mandelic acid
Mandelic acid, D-
(-)-alpha-Hydroxyphenylacetic acid
(R)-alpha-Hydroxybenzeneacetic acid
(R)-Mandelsaeure
MFCD00064251
(R)-A-Hydroxyphenylacetic acid
PPL7YW1M9W
CHEMBL292411
DTXSID4046523
CHEBI:17656
(2R)-hydroxy(phenyl)acetic acid
Hydroxy-Phenyl-Acetic Acid Anion
(2R)-hydroxy(phenyl)ethanoic acid
mandelic_acid
mandelic-acid
RMN
(2R)-Hydroxyphenylacetic Acid ((R)-Mandelic Acid)
DTXCID2026523
R(-)-Mandelic Acid
(R)-(-)-Amygdalic Acid
CAS-611-71-2
(R)-Hydroxy(phenyl)acetic acid
Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.R)-
UNII-PPL7YW1M9W
(L)-(+)-Mandelic acid
(-)-D-MANDELIC ACID
1mcz
1mdl
L-2-Hydroxy-2-phenylacetic acid
(-)-mandelate
NCGC00166022-01
d - mandelic acid
EINECS 210-276-6
D-2-Phenylglycolate
Sertraline impurity E
(-)-(R)-Mandelate
(r)(-)-mandelic acid
Benzeneacetic acid, alpha-hydroxy-, (-)-
Maybridge1_004148
(r)-(-) mandelic acid
(R)-(+)-mandelic acid
(R)-a-Hydroxyphenylacetate
(R)-Hydroxyphenylaceticacid
Benzeneacetic acid, alpha-hydroxy-, (alphaR)-
(-)-a-Hydroxyphenylacetate
(R)-a-Hydroxybenzeneacetate
Hydroxy-phenyl-acetate anion
(R)-(-)- mandelic acid
(r)-(-)-d-mandelic acid
Oprea1_502663
cid_11914
SCHEMBL165161
(-)-alpha-Hydroxyphenylacetate
(R)-alpha-Hydroxyphenylacetate
(-)-a-Hydroxyphenylacetic acid
(R)-alpha-Hydroxybenzeneacetate
(R)-a-Hydroxybenzeneacetic acid
BDBM16421
HMS553E14
HY-Y0585R
D,L-mandelic acid redetermination
D-(-)-Mandelic acid (Standard)
HMS3650C13
(R)-(-)-Mandelic acid, 98%
HY-Y0585
STR08136
Tox21_112292
s9003
(2R)-HYDROXYPHENYLACETIC ACID
AKOS005256699
Tox21_112292_1
(2R)-2-hydroxy-2-phenyl-acetic acid
AC-2490
CCG-266220
CS-W020074
DB02280
FM25007
(-)-(R)alpha-hydroxybenzeneacetic acid
(-)-(R) alpha-hydroxybenzeneacetic acid
NCGC00166022-02
(2R)-2-oxidanyl-2-phenyl-ethanoic acid
Benzeneacetic acid, alpha-hydroxy-, (R)-
M0662
NS00098847
(R)-.ALPHA.-HYDROXYBENZENEACETIC ACID
C01983
D70151
EN300-100159
MLS-0090888.0001
D-(-)-Mandelic acid, purum, >=98.0% (T)
D-(-)-Mandelic acid, puriss., >=99.0% (T)
SR-01000946767
(R)-(-)-Mandelic acid, ReagentPlus(R), >=99%
SR-01000946767-1
Q63390533
(R)-(-)-Mandelic acid, Vetec(TM) reagent grade, 98%
F1905-7046
SERTRALINE HYDROCHLORIDE IMPURITY E [EP IMPURITY]
Z1255390767
08C65DF7-6DDF-44B3-9490-02A43D9D33C1
(R)-(-)-Mandelic acid, ChiPros(R), produced by BASF, 99%
Sertraline impurity E, European Pharmacopoeia (EP) Reference Standard
(R)-a-Hydroxy-benzeneacetic acid;(R)-2-Hydroxy-2-phenylacetic acid;(R)-2-Phenylglycolic acid
Solubility of (2R)-2-hydroxy-2-phenyl-acetic acid
(2R)-2-hydroxy-2-phenyl-acetic acid, commonly known as mandelic acid, exhibits interesting solubility characteristics that are influenced by its functional groups and molecular structure. This compound is:
In general, the solubility of (2R)-2-hydroxy-2-phenyl-acetic acid underscores the principle that molecular polarity plays a crucial role in determining a compound’s ability to dissolve. As it is often stated: "Like dissolves like." This means that polar compounds will more readily dissolve in polar solvents, which is very much the case for mandelic acid.
Furthermore, variations in temperature can significantly affect its solubility, often resulting in increased solubility at higher temperatures, thus making it a compound of interest in various applications, particularly in pharmaceuticals.