Oleandrose

Oleandrose
Names
	IUPAC name (3S,4S,5S)-4,5-Dihydroxy-3-methoxyhexanal
	Other names 2,6-Dideoxy-3-O-methyl-L-arabinohexose
Identifiers
CAS Number	13089-77-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:10423;
KEGG	C08237;
PubChem CID	5461155;
UNII	C9TRD5E7IQ;
	InChI InChI=1S/C7H14O4/c1-5(9)7(10)6(11-2)3-4-8/h4-7,9-10H,3H2,1-2H3/t5-,6-,7-/m0/s1 Key: GOYBREOSJSERKM-ACZMJKKPSA-N;
	SMILES C[C@@H]([C@@H]([C@H](CC=O)OC)O)O;
Properties
Chemical formula	C7H14O4
Molar mass	162.185 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Oleandrose is a type of carbohydrate with the chemical formula C₇H₁₄O₄. With a six-carbon chain, it is classified as a hexose. With two hydroxyl groups replaced with hydrogen atoms, it is a dideoxy sugar. The hydroxyl group at C3 is methylated.

Occurrence

Oleandrdose is found in the leaves of Nerium oleander and may contribute to the toxicity of the plant.^[1]^[2] Oleandrose is also a component of several naturally-occurring chemical compounds including the avermectins (emamectin, abamectins, ivermectin, and others), the macrolide antibiotic oleandomycin, and the cardiac glycoside oleandrin.

Laboratory syntheses of L-oleandrose^[3] and DL-oleandrose^[4] have been reported.

References

^ Siddiqui, Bina Shaheen; Khatoon, Nasima; Begum, Sabira; Farooq, Ahsana Dar; Qamar, Kehkashan; Bhatti, Huma Aslam; Ali, Syed Kashif (2012). "Flavonoid and cardenolide glycosides and a pentacyclic triterpene from the leaves of Nerium oleander and evaluation of cytotoxicity". Phytochemistry. 77: 238–244. Bibcode:2012PChem..77..238S. doi:10.1016/j.phytochem.2012.01.001. PMID 22281382.
^ Bakir Çilesizoğlu, Neşe; Yalçin, Emine; Çavuşoğlu, Kültiğin; Sipahi Kuloğlu, Selin (2022). "Qualitative and quantitative phytochemical screening of Nerium oleander L. Extracts associated with toxicity profile". Scientific Reports. 12 (1): 21421. Bibcode:2022NatSR..1221421B. doi:10.1038/s41598-022-26087-0. PMC 9742154. PMID 36504046.
^ Bredenkamp, Martin W.; Holzapfel, Cedric W.; Toerien, Francois (1992). "Alternative Syntheses of L-(-)-Oleandrose from L-Rhamnose¹Preparation of Glycals". Synthetic Communications. 22 (17): 2459–2477. doi:10.1080/00397919208021642.
^ Berti, G.; Catelani, G.; Colonna, F.; Monti, L. (1982). "A highly diastereoselective synthesis of dl-oleandrose". Tetrahedron. 38 (20): 3067–3072. doi:10.1016/0040-4020(82)80194-4.

[1] Siddiqui, Bina Shaheen; Khatoon, Nasima; Begum, Sabira; Farooq, Ahsana Dar; Qamar, Kehkashan; Bhatti, Huma Aslam; Ali, Syed Kashif (2012). "Flavonoid and cardenolide glycosides and a pentacyclic triterpene from the leaves of Nerium oleander and evaluation of cytotoxicity". Phytochemistry. 77: 238–244. Bibcode:2012PChem..77..238S. doi:10.1016/j.phytochem.2012.01.001. PMID 22281382.

[2] Bakir Çilesizoğlu, Neşe; Yalçin, Emine; Çavuşoğlu, Kültiğin; Sipahi Kuloğlu, Selin (2022). "Qualitative and quantitative phytochemical screening of Nerium oleander L. Extracts associated with toxicity profile". Scientific Reports. 12 (1): 21421. Bibcode:2022NatSR..1221421B. doi:10.1038/s41598-022-26087-0. PMC 9742154. PMID 36504046.

[3] Bredenkamp, Martin W.; Holzapfel, Cedric W.; Toerien, Francois (1992). "Alternative Syntheses of L-(-)-Oleandrose from L-Rhamnose¹Preparation of Glycals". Synthetic Communications. 22 (17): 2459–2477. doi:10.1080/00397919208021642.

[4] Berti, G.; Catelani, G.; Colonna, F.; Monti, L. (1982). "A highly diastereoselective synthesis of dl-oleandrose". Tetrahedron. 38 (20): 3067–3072. doi:10.1016/0040-4020(82)80194-4.

[1]

[2]

[3]

[4]

Occurrence

See also

References