CAS 99-18-3

Prunasin

Description:

Prunasin is a cyanogenic glycoside, a type of compound that can release cyanide upon hydrolysis. It is primarily found in certain plants, particularly in the seeds of fruits such as cherries and almonds. The molecular formula of prunasin is C11H15NO6, and it has a relatively low molecular weight. This compound is characterized by its sweet taste, which is attributed to its sugar moiety, and its potential toxicity due to the release of cyanide, making it important to handle with care. Prunasin is soluble in water and can undergo enzymatic hydrolysis in the presence of specific enzymes, leading to the formation of benzaldehyde and hydrogen cyanide. Its presence in plants serves as a defense mechanism against herbivores. In terms of applications, prunasin is of interest in research related to plant biochemistry and toxicology, as well as in the study of cyanogenic compounds in food safety. Overall, while prunasin has potential uses in various fields, its toxic properties necessitate caution in its handling and consumption.

Formula: C₁₄H₁₇NO₆

InChI: InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9-,10+,11+,12-,13+,14+/m0/s1

InChI key: InChIKey=ZKSZEJFBGODIJW-GMDXDWKASA-N

SMILES: O([C@@H](C#N)C1=CC=CC=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O

Synonyms:

• (2R)-Prunasin
• (R)-(beta-D-Glucopyranosyloxy)phenylacetonitrile
• (R)-Prunasin
• (R)-alpha-(beta-D-Glucopyranosyloxy)benzene-acetonitrile
• (αR)-α-(β-<span class="text-smallcaps">D</span>-Glucopyranosyloxy)benzeneacetonitrile
• <span class="text-smallcaps">D</span>-Prunasin
• Benzeneacetonitrile 7-O-β-<span class="text-smallcaps">D</span>-glucopyranoside
• Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-, (R)- (9CI)
• Benzeneacetonitrile, α-(β-<span class="text-smallcaps">D</span>-glucopyranosyloxy)-, (R)-
• Benzeneacetonitrile, α-(β-<span class="text-smallcaps">D</span>-glucopyranosyloxy)-, (αR)-
• Brn 0091509
• D-Mandelonitrile-beta-D-glucoside
• D-Prunasin
• Prunasin
• Benzeneacetonitrile, α-(β-D-glucopyranosyloxy)-, (R)-
• 5-17-07-00405 (Beilstein Handbook Reference)
• (αR)-α-(β-D-Glucopyranosyloxy)benzeneacetonitrile

Prunasin

CAS: 99-18-3

Prunasin is an inhibitor of DNA Polymerase beta, a hydrolysis product of d-mandelonitrile-beta-d-glucoside, a naturally occurring carcinogenic compound. prunasin is a cyanogenic glycoside that must be metabolized to release cyanide and produces benzaldehyde upon hydrolysis.

Formula: C₁₄H₁₇NO₆

Purity: 99.69%

Color and Shape: Solid

Molecular weight: 295.2879

Ref: TM-TN2110

Prunasin

CAS: 99-18-3

Prunasin

Purity: ≥95%

Ref: 54-OR1037119

(R)-Prunasin

CAS: 99-18-3

Formula: C₁₄H₁₇NO₆

Molecular weight: 295.29

Ref: 4Z-P-115001

Prunasin

CAS: 99-18-3

Formula: C₁₄H₁₇NO₆

Purity: 95%~99%

Color and Shape: Powder

Molecular weight: 295.291

Ref: BP-SBP02178

Prunasin

CAS: 99-18-3

Formula: C₁₄H₁₇NO₆

Purity: 93%

Color and Shape: Solid

Molecular weight: 295.2879

Ref: IN-DA005T0C

(R)-Prunasin

CAS: 99-18-3

Stability Hygroscopic
Applications Used in the synthesis of cyanogen glycoside. A component of antiperspirants, deodorants, body soaps, shampoos, hair rinses, and hair; it inhibits volatile steroid formation by resident bacteria.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Marouf, A., et al.: Pharm. Biol., 39, 263 (2001), Fukuda, T., et al.: Biol. Pharm. Bull., 26, 271 (2003), Butler, M., et al.: J. Nat. Prod., 67, 2141 (2004), He, J., et al.: J. Nat. Prod., 69, 121 (2006),

Formula: C₁₄H₁₇NO₆

Color and Shape: Neat

Molecular weight: 295.29

Ref: TR-P839000

Prunasin

CAS: 99-18-3

(R)-2-Phenyl-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetonitrile

Formula: C₁₄H₁₇NO₆

Purity: 93%

Molecular weight: 295.29

Ref: IN-DG298213

(R)-Prunasin

CAS: 99-18-3

Formula: C₁₄H₁₇NO₆

Color and Shape: Solid

Molecular weight: 295.29

Ref: BE-RMT10206

R-Prunasin

CAS: 99-18-3

R-Prunasin is a cyanogenic glycoside, which is a naturally occurring compound found in certain plants. It is primarily sourced from species within the Prunus genus, such as cherries and almonds. The mode of action of R-Prunasin involves its enzymatic hydrolysis by beta-glucosidase, leading to the release of hydrogen cyanide, benzaldehyde, and glucose. This reaction is a classical example of plant defense mechanisms against herbivores and pathogens.

Formula: C₁₄H₁₇NO₆

Purity: Min. 95%

Color and Shape: White/Off-White Solid

Molecular weight: 295.29 g/mol

Ref: 3D-FP27250