4455. Glucoheptonic Acid

Nomenclature

CAS number: 87-74-1
d-glycero-d-gulo-Heptonic acid; α-glucoheptonic acid; glucosemonocarboxylic acid; glucomonocarbonic acid.
C7H14O8; mol wt 226.18.
C 37.17%, H 6.24%, O 56.59%.

Description and references

Obtained by treating glucose with HCN yielding a cyanohydrin which is saponified to glucoheptonic acid: Kiliani, Ber. 19, 769 (1886); Fischer, Ann. 270, 71 (1892); Armestar, C.A. 45, 2865 (1951). Process starting with calcium cyanide and glucose: Clevenot, US 2735866 (1956 to Lab. Clevenot). Diagnostic use of 99mTc complexes in renal scintigraphy: R. E. Boyd et al., Br. J. Radiol. 46, 604 (1973); in brain scanning: J. Léveillé et al., J. Nucl. Med. 18, 957 (1977); T. W. Ryerson et al., Radiology 127, 429 (1978). Subacute toxicity study: L. Belbeck et al., Can. J. Comp. Med. 45, 299 (1981).

Chemical structure

Properties

Lactonizes upon evapn. The lactone forms large sweetish crystals, mp 145-148°. [α]D20 56.0° (shows mutarotation). Sol in water.

Derivative

Sodium salt.

Nomenclature

CAS number: 13007-85-7
Gluceptate sodium; sodium glucoheptonate.
C7H13NaO8; mol wt 248.16.
C 33.88%, H 5.28%, Na 9.26%, O 51.58%.

Description and references

Prepn from corn syrup: Behnke, US 3022343 (1962 to Pfanstiehl Labs).

Properties

Crystals (α-form), dec 161°. [α]D20 +6.06° (c = 10 in H2O). Freely sol in water.

Derivative

Calcium salt.

Nomenclature

Gluceptate calcium; calcium glucoheptonate; calcium glucosemonocarbonate; calcium glucomonocarbonate; Calciforte (Serolam); Calheptose.
C14H26CaO16; mol wt 490.42.
C 34.29%, H 5.34%, Ca 8.17%, O 52.20%.

Description and references

Prepn from Na salt: Holstein, US 3033900 (1962 to Pfanstiehl Labs.).

Properties

Hygroscopic crystals, somewhat acrid taste, dec 200°. Sol in water.

Derivative

Magnesium salt.

Nomenclature

Magnesium glucoheptonate; magnesium glucosemonocarbonate; magnesium glucomonocarbonate; Navolin.
C14H26MgO16; mol wt 474.65.
C 35.43%, H 5.52%, Mg 5.12%, O 53.93%.

Description and references

Prepn: Cipelli, US 3063896 (1962 to Merck & Co.).

Properties

Water-sol crystals, pleasant taste.

Derivative

Complex with 99mTc.

Nomenclature

Technetium 99mTc gluceptate; technetium 99mTc gluheptonate; Glucoscan (DuPont); TechneScan gluceptate (Mallinckrodt).

Use

Pharmaceutic aid.

Therapeutic Category

99mTc complex as diagnostic aid (radioactive imaging agent).

Keywords

Technetium 99mTc Gluceptate: Diagnostic Aid (Radioactive Imaging Agent)