Calcium D-glucarate

Calcium D-glucarate
Names
	Other names Calcium d-saccharate, Antacidin
Identifiers
CAS Number	5793-88-4; tetrahydrate: 5793-89-5;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2104217;
ChemSpider	136477; tetrahydrate: 10128632;
DrugBank	DB13962;
ECHA InfoCard	100.024.850
EC Number	227-334-1; tetrahydrate: 611-592-0;
KEGG	tetrahydrate: D03307;
PubChem CID	154911; tetrahydrate: 11954337;
UNII	SST07NLK7J; tetrahydrate: 6AP9J91K4V;
CompTox Dashboard (EPA)	DTXSID70227186 ;
	InChI InChI=1S/C6H10O8.Ca/c7-1(3(9)5(11)12)2(8)4(10)6(13)14;/h1-4,7-10H,(H,11,12)(H,13,14);/q;+2/p-2/t1-,2-,3-,4+;/m0./s1 Key: UGZVNIRNPPEDHM-SBBOJQDXSA-L; tetrahydrate: InChI=1S/C6H10O8.Ca.4H2O/c7-1(3(9)5(11)12)2(8)4(10)6(13)14;;;;;/h1-4,7-10H,(H,11,12)(H,13,14);;4*1H2/q;+2;;;;/p-2/t1-,2-,3-,4+;;;;;/m0...../s1 Key: ZQWFSIZRQANUDA-WQMSYZFBSA-L;
	SMILES [C@H]([C@@H]([C@@H](C(=O)[O-])O)O)([C@H](C(=O)[O-])O)O.[Ca+2];
Properties
Chemical formula	C6H8CaO8
Molar mass	248.200 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

Calcium D-glucarate (or calcium saccharate) is the calcium salt of D-glucaric acid (saccharic acid), a substance naturally found in small amounts in fruits and vegetables such as oranges, apples, grapefruits, and cruciferous vegetables.^[1]^[2] It is commonly used as a dietary supplement, primarily marketed for its potential role in supporting detoxification processes and hormone regulation.^[2]^[3]

Structure and chemistry

Calcium D-glucarate is composed of calcium bound to D-glucaric acid, a derivative of glucose metabolism.^[4] D-Glucaric acid itself is classified as a sugar acid, and when bonded with calcium, it forms a more stable compound suitable for supplementation.

Biological activity

In the body, calcium D-glucarate is hydrolyzed to release D-glucaric acid, which can be further metabolized into compounds such as D-glucaro-1,4-lactone.^[5] These metabolites are known to inhibit the enzyme beta-glucuronidase.^[5]^[6] Beta-glucuronidase is involved in the breakdown of glucuronides in the liver and intestines, a process that can release potentially harmful compounds back into circulation.^[6]

By inhibiting beta-glucuronidase, calcium D-glucarate is thought to promote the excretion of carcinogens, steroid hormones (such as estrogen), and other potentially toxic substances bound for elimination through the bile and urine.^[5]^[7]

Dietary sources

Although calcium D-glucarate itself is not abundant in foods, D-glucaric acid is naturally present in fruits and vegetables.^[1]^[2] Foods with notable amounts include:

Oranges
Apples
Grapefruit
Broccoli
Brussels sprouts

Supplement use

Calcium D-glucarate is available as an over-the-counter dietary supplement, typically in capsule or tablet form. Dosages used in supplements generally range from 200 mg to 1000 mg per serving.^[2]

Safety and side effects

Calcium D-glucarate appears to be well tolerated in humans when used at typical supplemental doses.^[7]^[8] Reported side effects are rare but may include mild gastrointestinal discomfort. No major toxicity concerns have been identified in available studies, although long-term human research is limited^[7]^[8]

References

^ ^a ^b Vieths, S.; Schöning, B.; Jankiewicz, A. (January 1993). "Occurrence of IgE binding allergens during ripening of apple fruits". Food and Agricultural Immunology. 5 (2): 93–105. doi:10.1080/09540109309354788. ISSN 0954-0105.
^ ^a ^b ^c ^d Schattner, Mark A; Willis, Holly J; Raykher, Alexandra; Brown, Patricia; Quesada, Ofelia; Scott, Burma; Shike, Moshe (2006). "Long-term Enteral Nutrition Facilitates Optimization of Body Weight". Oncology & Hematology Review (US) (2): 104. doi:10.17925/ohr.2006.00.02.104. ISSN 2052-3815.
^ Ershow, Abby; Skeaff, Sheila; Merkel, Joyce; Pehrsson, Pamela (2018-01-17). "Development of Databases on Iodine in Foods and Dietary Supplements". Nutrients. 10 (1): 100. doi:10.3390/nu10010100. ISSN 2072-6643. PMC 5793328. PMID 29342090.
^ Walaszek, Z. (October 1990). "Potential use of d-glucaric acid derivatives in cancer prevention". Cancer Letters. 54 (1–2): 1–8. doi:10.1016/0304-3835(90)90083-a. ISSN 0304-3835. PMID 2208084.
^ ^a ^b ^c Walaszek, Zbigniew; Hanausek-Walaszek, Malgorzata; Webb, Thomas E. (1984). "Inhibition of 7,12-dimethylbenzanthracene-induced rat mammary tumorigenesis by 2,5-di-O-acetyl-D-glucaro-1, 4:6,3-dilactone, an in vivo β-glucuronidase inhibitor". Carcinogenesis. 5 (6): 767–772. doi:10.1093/carcin/5.6.767. ISSN 0143-3334. PMID 6202433.
^ ^a ^b Pasqualini, J.R.; Gelly, C. (April 1990). "Biological response of the anti-estrogen ICI 164,384 in human hormone-dependent and hormone-independent mammary cancer cell lines". Cancer Letters. 50 (2): 133–139. doi:10.1016/0304-3835(90)90243-q. ISSN 0304-3835. PMID 2328482.
^ ^a ^b ^c Crowell, Pamela L. (November 1997). "Monoterpenes in breast cancer chemoprevention". Breast Cancer Research and Treatment. 46 (2–3): 191–197. doi:10.1023/a:1005939806591. ISSN 0167-6806. PMID 9478274.
^ ^a ^b Whyte, Ian M. (January 2002). "Introduction: Research in Clinical Toxicology—The Value of High Quality Data". Journal of Toxicology: Clinical Toxicology. 40 (3): 211–212. doi:10.1081/clt-120005490. ISSN 0731-3810. PMID 12144193.

[:0-1] Vieths, S.; Schöning, B.; Jankiewicz, A. (January 1993). "Occurrence of IgE binding allergens during ripening of apple fruits". Food and Agricultural Immunology. 5 (2): 93–105. doi:10.1080/09540109309354788. ISSN 0954-0105.

[:1-2] Schattner, Mark A; Willis, Holly J; Raykher, Alexandra; Brown, Patricia; Quesada, Ofelia; Scott, Burma; Shike, Moshe (2006). "Long-term Enteral Nutrition Facilitates Optimization of Body Weight". Oncology & Hematology Review (US) (2): 104. doi:10.17925/ohr.2006.00.02.104. ISSN 2052-3815.

[3] Ershow, Abby; Skeaff, Sheila; Merkel, Joyce; Pehrsson, Pamela (2018-01-17). "Development of Databases on Iodine in Foods and Dietary Supplements". Nutrients. 10 (1): 100. doi:10.3390/nu10010100. ISSN 2072-6643. PMC 5793328. PMID 29342090.

[4] Walaszek, Z. (October 1990). "Potential use of d-glucaric acid derivatives in cancer prevention". Cancer Letters. 54 (1–2): 1–8. doi:10.1016/0304-3835(90)90083-a. ISSN 0304-3835. PMID 2208084.

[:2-5] Walaszek, Zbigniew; Hanausek-Walaszek, Malgorzata; Webb, Thomas E. (1984). "Inhibition of 7,12-dimethylbenzanthracene-induced rat mammary tumorigenesis by 2,5-di-O-acetyl-D-glucaro-1, 4:6,3-dilactone, an in vivo β-glucuronidase inhibitor". Carcinogenesis. 5 (6): 767–772. doi:10.1093/carcin/5.6.767. ISSN 0143-3334. PMID 6202433.

[:3-6] Pasqualini, J.R.; Gelly, C. (April 1990). "Biological response of the anti-estrogen ICI 164,384 in human hormone-dependent and hormone-independent mammary cancer cell lines". Cancer Letters. 50 (2): 133–139. doi:10.1016/0304-3835(90)90243-q. ISSN 0304-3835. PMID 2328482.

[:4-7] Crowell, Pamela L. (November 1997). "Monoterpenes in breast cancer chemoprevention". Breast Cancer Research and Treatment. 46 (2–3): 191–197. doi:10.1023/a:1005939806591. ISSN 0167-6806. PMID 9478274.

[:7-8] Whyte, Ian M. (January 2002). "Introduction: Research in Clinical Toxicology—The Value of High Quality Data". Journal of Toxicology: Clinical Toxicology. 40 (3): 211–212. doi:10.1081/clt-120005490. ISSN 0731-3810. PMID 12144193.

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